Substituted 4-benzoylpyrazoles

ABSTRACT

The invention relates to 4-benzoylpyrazoles of the formula I and their agriculturally useful salts thereof, processes and intermediates; compositions thereof; and use thereof for controlling undesireable plants.

This application is a 371 of PCT/EP97/07210 Dec. 19, 1997.

The present invention relates to substituted 4-benzoylpyrazoles of theformula I ##STR1## where the variables have the following meanings: R¹,R² are hydrogen, nitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆-alkynyl, --OR⁵, --OCOR⁶, --OSO₂ R⁶, --SH, --S(O)_(n) R⁷, --SO₂ OR⁵,--SO₂ NR⁵ R⁸, --NR⁸ SO₂ R⁶ or --NR⁸ COR⁶ ;

R³ is hydrogen, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, --OR⁷, --SR⁷ or--NR⁷ R¹⁰ ;

R⁴ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -alkenyl, C₄-C₆ -cycloalkenyl, C₃ -C₆ -alkynyl, --COR⁹, --CO₂ R⁹, --COSR⁹ or --CONR⁸R⁹, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl,cycloalkenyl and alkynyl radicals and R⁹ of the radicals --COR⁹, --CO₂R⁹, --COSR⁹ and --CONR⁸ R⁹ to be partially or fully halogenated and/orto have attached to them one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R¹⁰, --OR¹⁰, --SR¹⁰, --NR⁸ R¹⁰,═NOR¹⁰, --OCOR¹⁰, --SCOR¹⁰, --NR⁸ COR¹⁰, --CO₂ R¹⁰, --COSR¹⁰, --CONR⁸R¹⁰, C₁ -C₄ -alkyliminooxy, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkylcarbonyl,C₁ -C₄ -alkoxy-C₂ -C₆ -alkoxycarbonyl, C₁ -C₄ -alkylsulfonyl,heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy,benzyloxy and hetaryloxy, it being possible for the eight last-mentionedradicals, in turn, to be substituted;

X is oxygen or NR⁸ ;

n is 0, 1 or 2;

R⁵ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₂ -C₆-alkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl;

R⁶ is C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl;

R⁷ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₃-C₆ -alkenyl or C₃ -C₆ -alkynyl;

R⁸ is hydrogen or C₁ -C₆ -alkyl;

R⁹ is C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, phenyl or benzyl;

R¹⁰ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆-alkynyl;

Q is a pyrazole of the formula II ##STR2## which is linked in the4-position and where R¹¹ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, phenyl orphenyl which is partially or fully halogenated and/or has attached to itone to three of the following radicals:

nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy;

R¹² is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆-alkylcarbonyl, C₁ -C₆ -haloalkylcarbonyl, C₁ -C₆ -alkoxycarbonyl, C₁-C₆ -alkylsulfonyl, C₁ -C₆ -haloalkylsulfonyl, phenylcarbonyl,phenylcarbonylmethyl, phenoxycarbonyl or phenylsulfonyl, the fourlast-mentioned substituents being unsubstituted or the phenyl ring beingin each case partially or fully halogenated and/or having attached to itone to three of the following radicals:

nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy;

R¹³ is hydrogen, C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl;

and agriculturally useful salts thereof.

Moreover, the invention relates to processes and intermediates for thepreparation of compounds of the formula I, to compositions whichcomprise the latter, and to the use of the compounds of the formula Iand of the compositions comprising them for controlling weeds.

4-Benzoylpyrazoles are disclosed in the literature, for example in EP-A282 944.

However, the herbicidal properties of the prior-art compounds and thecrop plant tolerances are only partly satisfactory. It was an object ofthe present invention to find novel, in particular herbicidally active,compounds with improved properties.

This object is achieved by the 4-benzoylpyrazoles of the formula I andby their herbicidal activity.

Furthermore, there have been found herbicidal compositions whichcomprise the compounds I and which have a very good herbicidal activity.In addition, there have been found processes for the preparation ofthese compositions and methods of controlling undesirable vegetationusing the compounds I.

The present invention also relates to stereoisomers of the compounds ofthe formula I. These include pure stereoisomers and mixtures of these.

The compounds of the formula I contain a carbon-nitrogen double bond andtherefore exist in the form of E isomers or Z isomers or E/Z isomermixtures. Furthermore, the compounds of the formula I may containfurther carbon or carbon-nitrogen double bonds. The invention relatesboth to the pure geometric isomers and to mixtures of these.

Depending on the substitution pattern, the compounds of the formula Imay contain one or more chiral centers, in which case they exist in theform of enantiomers or diastereomer mixtures.

The invention relates both to the pure enantiomers or diastereomers andto the mixtures of these.

The compounds of the formula I may also be present in the form of theiragriculturally useful salts, the type of salt generally being of noimportance. In general, suitable salts are salts of those cations, orthe acid addition salts of those acids, whose cations, or anions,respectively, do not adversely affect the herbicidal activity of thecompounds I.

Suitable cations are, in particular, ions of the alkali metals,preferably lithium, sodium and potassium, of the alkaline earth metals,preferably calcium and magnesium, and of the transition metals,preferably manganese, copper, zinc and iron, and also ammonium where, ifdesired, one to four hydrogen atoms may be replaced by C₁ -C₄ -alkyl orhydroxy-C₁ -C₄ -alkyl and/or a phenyl or benzyl, preferablydiisopropylammonium, tetramethylammonium, tetrabutylammonium,trimethylbenzylammonium, moreover phosphonium ions, sulfonium ions,preferably tri(C₁ -C₄ -alkyl)sulfonium, and sulfoxonium ions, preferablytri(C₁ -C₄ -alkyl)sulfoxonium.

Anions of useful acid addition salts are mainly chloride, bromide,fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogenphosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate,hexafluorophosphate, benzoate and the anions of C₁ -C₄ -alkanoic acids,preferably formate, acetate, propionate and butyrate.

Special mention must be made of the compounds of the formula I accordingto the invention where

R⁴ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -alkenyl, C₄-C₆ -cycloalkenyl, C₃ -C₆ -alkynyl, --COR⁹, --CO₂ R⁹, --COSR⁹ or --CONR⁸R⁹, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl,cycloalkenyl and alkynyl radicals and R⁹ of the radicals --COR⁹, --CO₂R⁹, --COSR⁹ and --CONR⁸ R⁹ to be partially or fully halogenated and/orto have attached to them one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R¹⁰, --OR¹⁰, --SR¹⁰, --NR⁸ R¹⁰,═NOR¹⁰, --OCOR¹⁰, --SCOR¹⁰, --NR⁸ COR¹⁰, --CO₂ R¹⁰, --COSR¹⁰, --CONR⁸R¹⁰, C₁ -C₄ -alkyliminooxy, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkylcarbonyl,C₁ -C₄ -alkoxy-C₂ -C₆ -alkoxycarbonyl, C₁ -C₄ -alkylsulfonyl,heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy,benzyloxy and hetaryloxy, it being possible for the eight last-mentionedradicals, in turn, to be partially or fully halogenated and/or to haveattached to them one to three radicals from the following group:

nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkoxycarbonyl.

The organic moieties mentioned for the substituents R¹ -R¹³ or asradicals on phenyl, hetaryl and heterocyclyl rings are collective termsfor individual enumerations of the individual group members. Allhydrocarbon chains, ie. all alkyl, haloalkyl, cycloalkyl, alkoxyalkyl,alkoxy, haloalkoxy, alkyliminooxy, alkoxyamino, alkylsulfonyl,haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl,alkoxyalkoxycarbonyl, alkenyl, cycloalkenyl, alkynyl moieties can bestraight-chain or branched. Unless otherwise specified, halogenatedsubstituents preferably have attached to them one to five identical ordifferent halogen atoms, the meaning halogen being in each casefluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C₂ -C₄ -alkyl: ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl and 1,1-dimethylethyl;

C₁ -C₄ -alkyl, and the alkyl moieties of C₁ -C₄ -alkylcarbonyl: C₂ -C₄-alkyl as mentioned above and also methyl;

C₂ -C₆ -alkyl and the alkyl moieties of C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl: C₂-C₄ -alkyl as mentioned above, and also pentyl, 1-methylbutyl,2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;

C₁ -C₆ -alkyl and the alkyl moieties of C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl andC₁ alkyl C₆ -alkylcarbonyl: C₂ alkyl C₆ -alkyl as mentioned above, andalso methyl;

C₁ -C₄ -haloalkyl: a C₁ alkyl C₄ -alkyl radical as mentioned above whichis partially or fully substituted by fluorine, chlorine, bromine and/oriodine, eg. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl,difluoromethyl, trifluoromethyl, chlorofluoromethyl,dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl,2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl,2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl,2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl,1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyland nonafluorobutyl;

C₁ alkyl C₆ -haloalkyl and the haloalkyl moieties of C₁ -C₆-haloalkylcarbonyl: C₁ -C₄ -haloalkyl as mentioned above, and also5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,6-iodohexyl and dodecafluorohexyl;

C₁ -C₄ -alkoxy and the alkoxy moieties of C₁ -C₄ -alkoxyamino, C₁ -C₄-alkoxy-C₂ alkyl C₆ -alkoxycarbonyl and C₁ -C₄ -alkoxycarbonyl: methoxy,ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy,2-methylpropoxy and 1,1-dimethylethoxy;

C₁ alkyl C₆ -alkoxy and the alkoxy moieties of C₁ -C₆ -alkoxy-C₁ -C₆-alkyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₁ -C₄ -alkoxy-C₂ -C₆-alkoxycarbonyl and C₁ -C₆ -alkoxycarbonyl: C₁ -C₄ -alkoxy as mentionedabove, and also pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy,1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxyand 1-ethyl-2-methylpropoxy;

C₁ -C₄ -haloalkoxy: a C₁ -C₄ -alkoxy radical as mentioned above which ispartially or fully substituted by fluorine, chlorine, bromine and/oriodine, eg. fluoromethoxy, difluoromethoxy, trifluoromethoxy,chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy,2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy,3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy,1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy,4-bromobutoxy and nonafluorobutoxy;

C₁ -C₄ -alkylsulfonyl (C₁ -C₄ -alkyl-S(═O)₂ --): methylsulfonyl,ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl,1-methylpropylsulfonyl, 2-methylpropylsulfonyl and1,1-dimethylethylsulfonyl;

C₁ -C₆ -alkylsulfonyl: C₁ -C₄ -alkylsulfonyl as mentioned above, andalso pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl,1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl,1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl,1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl,1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl,2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl,1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl,1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl,1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C₁ -C₆ -haloalkylsulfonyl: a C₁ -C₆ -alkylsulfonyl radical as mentionedabove which is partially or fully substituted by fluorine, chlorine,bromine and/or iodine, ie. fluoromethylsulfonyl, difluoromethylsulfonyl,trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl,bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl,2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl,2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,2,2,2-trichloroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl,2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl,3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl,2-bromopropylsulfonyl, 3-bromopropylsulfonyl,2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl,heptafluoropropyl-sulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl,1-(choromethyl)-2-chloroethylsulfonyl,1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl,5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl,5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl,6-iodohexylsulfonyl and dodecafluorohexylsulfonyl;

C₁ -C₄ -alkyliminooxy: methyliminooxy, ethyliminooxy, 1-propyliminooxy,2-propyliminooxy, 1-butyliminooxy and 2-butyliminooxy;

C₃ -C₆ -alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl,buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl,2-mnethylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl,penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl,1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl,1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1yl,3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl ,1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl,1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl,hex-4-en-1-yl, hex5-en-1-yl, 1-methylpent-1-en-1-yl,2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl,1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl,4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl,2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl,1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl,1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl,2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl,3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl,1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl,1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl;

C₂ -C₆ -alkenyl: C₃ -C₆ -alkenyl as mentioned above, and also ethenyl;

C₃ -C₆ -alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn-1-yl,but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-1-yl,pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl,pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl,3-methylbut-1-yn-4-yl, hex-1-yn-1-yl, hex-1-yn-3-yl, hex-1-yn-4-yl,hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl,hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl,3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl,3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yland 4-methylpent-2-yn-5-yl;

C₂ -C₆ -alkynyl: C₃ -C₆ -alkynyl as mentioned above, and also ethynyl:

C₃ -C₆ -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C₄ -C₆ -cycloalkenyl: cyclobuten-1-yl, cyclobuten-3-yl,cyclopenten-1-yl, cyclopenten-3-yl, cyclopenten-4-yl, cyclohexen-1-yl,cyclohexen-3-yl and cyclohexen-4-yl;

heterocyclyl, and also the heterocyclyl radicals in heterocyclyloxy:three- to seven-membered saturated or partially unsaturated mono- orpolycyclic heterocycles which contain one to three hetero atoms selectedfrom a group consisting of oxygen, nitrogen and sulfur, such asoxiranyl, oxetan-3-yl, thietan-3-yl, 2-tetrahydrofuranyl,3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl,2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl,2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,3-dihydrofuran-4-yl,2,3-dihydrofuran-5-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl,2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl,2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl,2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl,2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl,2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl,4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl,2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl,2,5-dihydroxazol-5-yl, 2,3-dihydroisothiazol-3-yl,2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl,4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl,4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl,2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl,2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,2,3-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl,4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl,2,5-dihydropyrazol-3-yl, 2,5-dihydropyrazol-4-yl,2,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl,2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl,4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl,2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl,2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl,4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl,4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl,2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl,2,3-dihydroitidazol-2-yl, 2,3-dihydroitidazol-4-yl,2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl,4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl,2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl,2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl,3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl,4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl,4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl,1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl,1,3-dihydrooxazin-2-yl, 1,3-dioxan-2-yl, 1,3-dithian-2-yl,2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl,2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl,4-tetrahydrothiopyranyl, 1,3-dioxolan-2-yl, 1,3-dithiolan-2-yl,3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl,4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl,2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl,1,3-dihydrooxazin-2-yl,

hetaryl, and also the hetaryl radicals in hetaryloxy: aromatic mono- orpolycyclic radicals which, besides carbon ring members, may additionallycontain one to four nitrogen atoms or one to three nitrogen atoms andone oxygen or one sulfur atom or one oxygen or one sulfur atom, eg.2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl,2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl,5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl,1,2,4,5-tetrazin-3-yl, and also the corresponding benzofuzedderivatives.

All phenyl, hetaryl and heterocyclyl rings are preferably unsubstitutedor have attached to them one to three halogen atoms and/or one or tworadicals selected from the following group: nitro, cyano, methyl,trifluoromethyl, methoxy, trifluoromethoxy or methoxycarbonyl.

With a view to the use of the compounds of the formula I according tothe invention as herbicides, the variables preferably have the followingmeanings, viz. in each case alone or in combination:

R¹ is nitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆-haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆-alkynyl, --OR⁵ or --S(O)_(n) R⁷ ;

especially preferably nitro, halogen, eg. fluorine, chlorine or bromine,C₁ -C₆ -haloalkyl, --OR⁵ or --SO₂ R⁷, eg. methylsulfonyl, ethylsulfonylor difluoromethylsulfonyl; particularly preferably nitro, fluorine,chlorine, bromine, trifluoromethyl, methoxy, ethoxy, methylsulfonyl,ethylsulfonyl or difluoromethylsulfonyl;

R² is hydrogen, nitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁-C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆-alkynyl, --OR⁵ or --S(O)_(n) R⁷ ;

especially preferably hydrogen, nitro, halogen, eg. fluorine, chlorineor bromine, C₁ -C₆ -alkyl, eg. methyl or ethyl, C₁ -C₆ -haloalkyl, --OR⁵or --SO₂ R⁷, eg. methylsulfonyl, ethylsulfonyl ordifluoromethylsulfonyl;

particularly preferably nitro, fluorine, chlorine, bromine, methyl,ethyl, trifluoromethyl, methoxy, ethoxy, methylsulfonyl, ethylsulfonylor difluoromethylsulfonyl;

R³ is hydrogen, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl or --OR⁷ ;

R⁴ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -alkenyl or C₃-C₆ -alkynyl, it being possible for the 4 last-mentioned substituents tobe partially or fully halogenated and/or to have attached to them one tothree of the following groups: hydroxyl, mercapto, amino, cyano, --OR¹⁰,═NOR¹⁰, --OCOR¹⁰, --CO₂ R¹⁰, --COSR¹⁰, --CONR⁸ R¹⁰, C₁ -C₄-alkyliminooxy, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-C₂ -C₆-alkoxycarbonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl,phenoxy, benzyloxy or hetaryloxy, it being possible for the eightlast-mentioned radicals, in turn, to be partially or fully halogenatedand/or to contain one to three radicals selected from the followinggroup:

nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkoxycarbonyl;

particularly preferably C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆-alkenyl or C₃ -C₆ -alkynyl, it being possible for the 4 last-mentionedsubstituents to be partially or fully halogenated and/or to haveattached to them one to three of the following groups: hydroxyl,mercapto, amino, cyano, --OR¹⁰, ═NOR¹⁰, --OCOR¹⁰, --CO₂ R¹⁰, --COSR¹⁰,--CONR⁸ R¹⁰, C₁ -C₄ -alkyliminooxy, C₁ -C₄ -alkylcarbonyl, C₁ -C₄-alkoxy-C₂ -C₆ -alkoxycarbonyl, heterocyclyl, heterocyclyloxy, phenyl,benzyl, hetaryl, phenoxy, benzyloxy or hetaryloxy, it being possible forthe eight last-mentioned radicals, in turn, to be partially or fullyhalogenated and/or to contain one to three radicals selected from thefollowing group:

nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkoxycarbonyl;

X is oxygen or NH;

n is 0 or 2;

R⁵ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₂ -C₆-alkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl;

especially preferably methyl, ethyl, trifluoromethyl, difluoromethyl,methoxyethyl, allyl or propargyl;

R⁷ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₃-C₆ -alkenyl or C₃ -C₆ -alkynyl;

especially preferably methyl, ethyl, trifluoromethyl, difluoromethyl,methoxyethyl, allyl or propargyl;

R⁸ is hydrogen or C₁ -C₆ -alkyl;

R¹⁰ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆-alkynyl;

R¹¹ is C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl; especially preferably methyl,ethyl, propyl, isopropyl, butyl or isobutyl;

R¹² is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkylcarbonyl, C₁ -C₆-haloalkylcarbonyl, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylsulfonyl, C₁-C₆ -haloalkylsulfonyl, phenylcarbonylmethyl, or phenylsulfonyl, itbeing possible for the phenyl ring of the two last-mentionedsubstituents to be partially or fully halogenated and/or to haveattached to it one to three of the following radicals: nitro, cyano, C₁-C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy;

R¹³ is hydrogen, C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl; especiallypreferably hydrogen, methyl, ethyl or trifluoromethyl.

Particularly preferred are compounds of the formula Ia (=I where R¹ isbonded in the 4-position of the phenyl ring and R² in the 2-position ofthe phenyl ring). ##STR3##

Extraordinarily preferred are the compounds of the formula Ia where thevariables R¹ to R³, Q and X have the abovementioned meanings and

R⁴ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -alkenyl or C₃-C₆ -alkynyl, it being possible for the 4 last-mentioned substituents tobe partially or fully halogenated and/or to have attached to them one tothree of the following groups: hydroxyl, mercapto, amino, cyano, --OR¹⁰,═NOR¹⁰, --OCOR¹⁰, --CO₂ R¹⁰, --COSR¹⁰, --CONR⁸ R¹⁰, C₁ -C₄-alkyliminooxy, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-C₂ -C₆-alkoxycarbonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl,phenoxy, benzyloxy or hetaryloxy, it being possible for the eightlast-mentioned radicals, in turn, to be partially or fully halogenatedand/or to have attached to them one to three radicals selected from thefollowing group:

nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy, C₁ -C₄ -alkoxycarbonyl.

Particularly extraordinarily preferred are the compounds Ia1 (=I whereR¹ ═Cl, R¹¹ ═CH₃ and R¹² and R¹³ ═H, where R¹ is bonded in the4-position of the phenyl ring and R² in the 2-position of the phenylring), in particular the compounds of Table 1.

                  TABLE 1                                                         ______________________________________                                                                       Ia1                                                                             #STR4##                                         -                                                                          No.      R.sup.2  R.sup.3   R.sup.4  X                                        ______________________________________                                        Ia1.001  Cl       H         CH.sub.3 O                                          Ia1.002            Cl           H                  C.sub.2 H.sub.5                                                 O                                        Ia1.003            Cl           H                  CH.sub.2 --C.tbd.CH                                           O                                          Ia1.004            Cl           CH.sub.3             CH.sub.3                                                         O                                     Ia1.005            Cl           CH.sub.3             C.sub.2 H.sub.5                                                 O                                      Ia1.006            Cl           CH.sub.3             CH.sub.2 --C.tbd.CH                                           O                                        Ia1.007            Cl           C.sub.2 H.sub.5     CH.sub.3                                                         O                                      Ia1.008            Cl           C.sub.2 H.sub.5     C.sub.2 H.sub.5                                                 O                                       Ia1.009            Cl           C.sub.2 H.sub.5     CH.sub.2 --C.tbd.CH                                           O                                         Ia1.010            Cl           OCH.sub.3            CH.sub.3                                                         O                                     Ia1.011            Cl           OCH.sub.3            C.sub.2 H.sub.5                                                 O                                      Ia1.012            Cl           OCH.sub.3            CH.sub.2 --C.tbd.CH                                           O                                        Ia1.013            Cl           OC.sub.2 H.sub.5    CH.sub.3                                                         O                                      Ia1.014            Cl           OC.sub.2 H.sub.5    C.sub.2 H.sub.5                                                 O                                       Ia1.015            Cl           OC.sub.2 H.sub.5    CH.sub.2 --C.tbd.CH                                           O                                         Ia1.016            Cl           H                  CH.sub.3                                                         NH                                      Ia1.017            Cl           H                  C.sub.2 H.sub.5                                                 NH                                       Ia1.018            Cl           H                  CH.sub.2 --C.tbd.CH                                           NH                                         Ia1.019            Cl           CH.sub.3            CH.sub.3                                                         NH                                     Ia1.020            Cl           CH.sub.3            C.sub.2 H.sub.5                                                 NH                                      Ia1.021            Cl           CH.sub.3            CH.sub.2 --C.tbd.CH                                           NH                                        Ia1.022            Cl           C.sub.2 H.sub.5    CH.sub.3                                                         NH                                      Ia1.023            Cl           C.sub.2 H.sub.5    C.sub.2 H.sub.5                                                 NH                                       Ia1.024            Cl           C.sub.2 H.sub.5    CH.sub.2 --C.tbd.CH                                           NH                                         Ia1.025            Cl           OCH.sub.3           CH.sub.3                                                         NH                                     Ia1.026            Cl           OCH.sub.3           C.sub.2 H.sub.5                                                 NH                                      Ia1.027            Cl           OCH.sub.3           CH.sub.2 --C.tbd.CH                                           NH                                        Ia1.028            Cl           OC.sub.2 H.sub.5   CH.sub.3                                                         NH                                      Ia1.029            Cl           OC.sub.2 H.sub.5   C.sub.2 H.sub.5                                                 NH                                       Ia1.030            Cl           OC.sub.2 H.sub.5   CH.sub.2 --C.tbd.CH                                           NH                                         Ia1.031           CH.sub.3           H                  CH.sub.3                                                          O                                 Ia1.032           CH.sub.3           H                  C.sub.2 H.sub.5                                                  O                                  Ia1.033           CH.sub.3           H                  CH.sub.2                                                 --C.tbd.CH   O                             Ia1.034           CH.sub.3           CH.sub.3            CH.sub.3                                                          O                                Ia1.035           CH.sub.3           CH.sub.3            C.sub.2                                                 H.sub.5         O                          Ia1.036           CH.sub.3           CH.sub.3            CH.sub.2                                                --C.tbd.CH   O                             Ia1.037           CH.sub.3           C.sub.2 H.sub.5    CH.sub.3                                                          O                                 Ia1.038           CH.sub.3           C.sub.2 H.sub.5    C.sub.2 H.sub.5                                                  O                                  Ia1.039           CH.sub.3           C.sub.2 H.sub.5    CH.sub.2                                                 --C.tbd.CH   O                             Ia1.040           CH.sub.3           OCH.sub.3           CH.sub.3                                                          O                                Ia1.041           CH.sub.3           OCH.sub.3           C.sub.2                                                 H.sub.5         O                          Ia1.042           CH.sub.3           OCH.sub.3           CH.sub.2                                                --C.tbd.CH   O                             Ia1.043           CH.sub.3           OC.sub.2 H.sub.5   CH.sub.3                                                          O                                 Ia1.044           CH.sub.3           OC.sub.2 H.sub.5   C.sub.2 H.sub.5                                                  O                                  Ia1.045           CH.sub.3           OC.sub.2 H.sub.5   CH.sub.2                                                 --C.tbd.CH   O                             Ia1.046           CH.sub.3           H                  CH.sub.3                                                         NH                                 Ia1.047           CH.sub.3           H                  C.sub.2 H.sub.5                                                 NH                                  Ia1.048           CH.sub.3           H                  CH.sub.2                                                 --C.tbd.CH  NH                             Ia1.049           CH.sub.3           CH.sub.3            CH.sub.3                                                         NH                                Ia1.050           CH.sub.3           CH.sub.3            C.sub.2                                                 H.sub.5        NH                          Ia1.051           CH.sub.3           CH.sub.3            CH.sub.2                                                --C.tbd.CH  NH                             Ia1.052           CH.sub.3           C.sub.2 H.sub.5    CH.sub.3                                                         NH                                 Ia1.053           CH.sub.3           C.sub.2 H.sub.5    C.sub.2 H.sub.5                                                 NH                                  Ia1.054           CH.sub.3           C.sub.2 H.sub.5    CH.sub.2                                                 --C.tbd.CH  NH                             Ia1.055           CH.sub.3           OCH.sub.3           CH.sub.3                                                         NH                                Ia1.056           CH.sub.3           OCH.sub.3           C.sub.2                                                 H.sub.5        NH                          Ia1.057           CH.sub.3           OCH.sub.3           CH.sub.2                                                --C.tbd.CH  NH                             Ia1.058           CH.sub.3           OC.sub.2 H.sub.5   CH.sub.3                                                         NH                                 Ia1.059           CH.sub.3           OC.sub.2 H.sub.5   C.sub.2 H.sub.5                                                 NH                                  Ia1.060           CH.sub.3           OC.sub.2 H.sub.5   CH.sub.2                                                 --C.tbd.CH  NH                             Ia1.061           OCH.sub.3          H                  CH.sub.3                                                          O                                 Ia1.062           OCH.sub.3          H                  C.sub.2 H.sub.5                                                  O                                  Ia1.063           OCH.sub.3          H                  CH.sub.2                                                 --C.tbd.CH   O                             Ia1.064           OCH.sub.3          CH.sub.3            CH.sub.3                                                          O                                Ia1.065           OCH.sub.3          CH.sub.3            C.sub.2                                                 H.sub.5         O                          Ia1.066           OCH.sub.3          CH.sub.3            CH.sub.2                                                --C.tbd.CH   O                             Ia1.067           OCH.sub.3          C.sub.2 H.sub.5    CH.sub.3                                                          O                                 Ia1.068           OCH.sub.3          C.sub.2 H.sub.5    C.sub.2 H.sub.5                                                  O                                  Ia1.069           OCH.sub.3          C.sub.2 H.sub.5    CH.sub.2                                                 --C.tbd.CH   O                             Ia1.070           OCH.sub.3          OCH.sub.3           CH.sub.3                                                          O                                Ia1.071           OCH.sub.3          OCH.sub.3           C.sub.2                                                 H.sub.5         O                          Ia1.072           OCH.sub.3          OCH.sub.3           CH.sub.2                                                --C.tbd.CH   O                             Ia1.073           OCH.sub.3          OC.sub.2 H.sub.5   CH.sub.3                                                          O                                 Ia1.074           OCH.sub.3          OC.sub.2 H.sub.5   C.sub.2 H.sub.5                                                  O                                  Ia1.075           OCH.sub.3          OC.sub.2 H.sub.5   CH.sub.2                                                 --C.tbd.CH   O                             Ia1.076           OCH.sub.3          H                  CH.sub.3                                                          NH                                Ia1.077           OCH.sub.3          H                  C.sub.2 H.sub.5                                                  NH                                 Ia1.078           OCH.sub.3          H                  CH.sub.2                                                 --C.tbd.CH   NH                            Ia1.079           OCH.sub.3          CH.sub.3            CH.sub.3                                                          NH                               Ia1.080           OCH.sub.3          CH.sub.3            C.sub.2                                                 H.sub.5         NH                         Ia1.081           OCH.sub.3          CH.sub.3            CH.sub.2                                                --C.tbd.CH   NH                            Ia1.082           OCH.sub.3          C.sub.2 H.sub.5    CH.sub.3                                                          NH                                Ia1.083           OCH.sub.3          C.sub.2 H.sub.5    C.sub.2 H.sub.5                                                  NH                                 Ia1.084           OCH.sub.3          C.sub.2 H.sub.5    CH.sub.2                                                 --C.tbd.CH   NH                            Ia1.085           OCH.sub.3          OCH.sub.3           CH.sub.3                                                          NH                               Ia1.086           OCH.sub.3          OCH.sub.3           C.sub.2                                                 H.sub.5         NH                         Ia1.087           OCH.sub.3          OCH.sub.3           CH.sub.2                                                --C.tbd.CH   NH                            Ia1.088           OCH.sub.3          OC.sub.2 H.sub.5   CH.sub.3                                                          NH                                Ia1.089           OCH.sub.3          OC.sub.2 H.sub.5   C.sub.2 H.sub.5                                                  NH                                 Ia1.090           OCH.sub.3          OC.sub.2 H.sub.5   CH.sub.2                                                 --C.tbd.CH   NH                            Ia1.091           CF.sub.3           H                  CH.sub.3                                                         O                                  Ia1.092           CF.sub.3           H                  C.sub.2 H.sub.5                                                 O                                   Ia1.093           CF.sub.3           H                  CH.sub.2                                                 --C.tbd.CH  O                              Ia1.094           CF.sub.3           CH.sub.3            CH.sub.3                                                         O                                 Ia1.095           CF.sub.3           CH.sub.3            C.sub.2                                                 H.sub.5        O                           Ia1.096           CF.sub.3           CH.sub.3            CH.sub.2                                                --C.tbd.CH  O                              Ia1.097           CF.sub.3           C.sub.2 H.sub.5    CH.sub.3                                                         O                                  Ia1.098           CF.sub.3           C.sub.2 H.sub.5    C.sub.2 H.sub.5                                                 O                                   Ia1.099           CF.sub.3           C.sub.2 H.sub.5    CH.sub.2                                                 --C.tbd.CH  O                              Ia1.100           CF.sub.3           OCH.sub.3           CH.sub.3                                                         O                                 Ia1.101           CF.sub.3           OCH.sub.3           C.sub.2                                                 H.sub.5        O                           Ia1.102           CF.sub.3           OCH.sub.3           CH.sub.2                                                --C.tbd.CH  O                              Ia1.103           CF.sub.3           OC.sub.2 H.sub.5   CH.sub.3                                                         O                                  Ia1.104           CF.sub.3           OC.sub.2 H.sub.5   C.sub.2 H.sub.5                                                 O                                   Ia1.105           CF.sub.3           OC.sub.2 H.sub.5   CH.sub.2                                                 --C.tbd.CH  O                              Ia1.106           CF.sub.3           H                  CH.sub.3                                                         NH                                 Ia1.107           CF.sub.3           H                  C.sub.2 H.sub.5                                                 NH                                  Ia1.108           CF.sub.3           H                  CH.sub.2                                                 --C.tbd.CH  NH                             Ia1.109           CF.sub.3           CH.sub.3            CH.sub.3                                                         NH                                Ia1.110           CF.sub.3           CH.sub.3            C.sub.2                                                 H.sub.5        NH                          Ia1.111           CF.sub.3           CH.sub.3            CH.sub.2                                                --C.tbd.CH  NH                             Ia1.112           CF.sub.3           C.sub.2 H.sub.5    CH.sub.3                                                         NH                                 Ia1.113           CF.sub.3           C.sub.2 H.sub.5    C.sub.2 H.sub.5                                                 NH                                  Ia1.114           CF.sub.3           C.sub.2 H.sub.5    CH.sub.2                                                 --C.tbd.CH  NH                             Ia1.115           CF.sub.3           OCH.sub.3           CH.sub.3                                                         NH                                Ia1.116           CF.sub.3           OCH.sub.3           C.sub.2                                                 H.sub.5        NH                          Ia1.117           CF.sub.3           OCH.sub.3           CH.sub.2                                                --C.tbd.CH  NH                             Ia1.118           CF.sub.3           OC.sub.2 H.sub.5   CH.sub.3                                                         NH                                 Ia1.119           CF.sub.3           OC.sub.2 H.sub.5   C.sub.2 H.sub.5                                                 NH                                  Ia1.120           CF.sub.3           OC.sub.2 H.sub.5   CH.sub.2                                                 --C.tbd.CH  NH                             Ia1.121          SO.sub.2 CH.sub.3         H                  CH.sub.3                                                         O                            Ia1.122          SO.sub.2 CH.sub.3         H                  C.sub.2                                            H.sub.5        O                           Ia1.123          SO.sub.2 CH.sub.3         H                  CH.sub.2                                           --C.tbd.CH  O                              Ia1.124          SO.sub.2 CH.sub.3         CH.sub.3            CH.sub.3                                                         O                           Ia1.125          SO.sub.2 CH.sub.3         CH.sub.3            C.sub.2                                           H.sub.5         O                          Ia1.126          SO.sub.2 CH.sub.3         CH.sub.3            CH.sub.2                                          --C.tbd.CH   O                             Ia1.127          SO.sub.2 CH.sub.3         C.sub.2 H.sub.5    CH.sub.3                                                          O                           Ia1.128          SO.sub.2 CH.sub.3         C.sub.2 H.sub.5    C.sub.2                                            H.sub.5         O                          Ia1.129          SO.sub.2 CH.sub.3         C.sub.2 H.sub.5    CH.sub.2                                           --C.tbd.CH   O                             Ia1.130          SO.sub.2 CH.sub.3         OCH.sub.3           CH.sub.3                                                          O                          Ia1.131          SO.sub.2 CH.sub.3         OCH.sub.3           C.sub.2                                           H.sub.5         O                          Ia1.132          SO.sub.2 CH.sub.3         OCH.sub.3           CH.sub.2                                          --C.tbd.CH   O                             Ia1.133          SO.sub.2 CH.sub.3         OC.sub.2 H.sub.5   CH.sub.3                                                          O                           Ia1.134          SO.sub.2 CH.sub.3         OC.sub.2 H.sub.5   C.sub.2                                            H.sub.5         O                          Ia1.135          SO.sub.2 CH.sub.3         OC.sub.2 H.sub.5   CH.sub.2                                           --C.tbd.CH   O                             Ia1.136          SO.sub.2 CH.sub.3         H                  CH.sub.3                                                          NH                          Ia1.137          SO.sub.2 CH.sub.3         H                  C.sub.2                                            H.sub.5         NH                         Ia1.138          SO.sub.2 CH.sub.3         H                  CH.sub.2                                           --C.tbd.CH   NH                            Ia1.139          SO.sub.2 CH.sub.3         CH.sub.3            CH.sub.3                                                          NH                         Ia1.140          SO.sub.2 CH.sub.3         CH.sub.3            C.sub.2                                           H.sub.5         NH                         Ia1.141          SO.sub.2 CH.sub.3         CH.sub.3            CH.sub.2                                          --C.tbd.CH   NH                            Ia1.142          SO.sub.2 CH.sub.3         C.sub.2 H.sub.5    CH.sub.3                                                          NH                          Ia1.143          SO.sub.2 CH.sub.3         C.sub.2 H.sub.5    C.sub.2                                            H.sub.5         NH                         Ia1.144          SO.sub.2 CH.sub.3         C.sub.2 H.sub.5    CH.sub.2                                           --C.tbd.CH   NH                            Ia1.145          SO.sub.2 CH.sub.3         OCH.sub.3           CH.sub.3                                                          NH                         Ia1.146          SO.sub.2 CH.sub.3         OCH.sub.3           C.sub.2                                           H.sub.5         NH                         Ia1.147          SO.sub.2 CH.sub.3         OCH.sub.3           CH.sub.2                                          --C.tbd.CH   NH                            Ia1.148          SO.sub.2 CH.sub.3         OC.sub.2 H.sub.5   CH.sub.3                                                          NH                          Ia1.149          SO.sub.2 CH.sub.3         OC.sub.2 H.sub.5   C.sub.2                                            H.sub.5         NH                         Ia1.150          SO.sub.2 CH.sub.3         OC.sub.2 H.sub.5   CH.sub.2                                           --C.tbd.CH   NH                            Ia1.151           NO.sub.2           H                  CH.sub.3                                                          O                                 Ia1.152           NO.sub.2           H                  C.sub.2 H.sub.5                                                  O                                  Ia1.153           NO.sub.2           H                  CH.sub.2                                                 --C.tbd.CH   O                             Ia1.154           NO.sub.2           CH.sub.3            CH.sub.3                                                         O                                 Ia1.155           NO.sub.2           CH.sub.3            C.sub.2                                                 H.sub.5        O                           Ia1.156           NO.sub.2           CH.sub.3            CH.sub.2                                                --C.tbd.CH  O                              Ia1.157           NO.sub.2           C.sub.2 H.sub.5    CH.sub.3                                                         O                                  Ia1.158           NO.sub.2           C.sub.2 H.sub.5    C.sub.2 H.sub.5                                                 O                                   Ia1.159           NO.sub.2           C.sub.2 H.sub.5    CH.sub.2                                                 --C.tbd.CH  O                              Ia1.160           NO.sub.2           OCH.sub.3           CH.sub.3                                                         O                                 Ia1.161           NO.sub.2           OCH.sub.3           C.sub.2                                                 H.sub.5        O                           Ia1.162           NO.sub.2           OCH.sub.3           CH.sub.2                                                --C.tbd.CH  O                              Ia1.163           NO.sub.2           OC.sub.2 H.sub.5   CH.sub.3                                                         O                                  Ia1.164           NO.sub.2           OC.sub.2 H.sub.5   C.sub.2 H.sub.5                                                 O                                   Ia1.165           NO.sub.2           OC.sub.2 H.sub.5   CH.sub.2                                                 --C.tbd.CH  O                              Ia1.166           NO.sub.2           H                  CH.sub.3                                                        NH                                  Ia1.167           NO.sub.2           H                  C.sub.2 H.sub.5                                                NH                                   Ia1.168           NO.sub.2           H                  CH.sub.2                                                 --C.tbd.CH NH                              Ia1.169           NO.sub.2           CH.sub.3            CH.sub.3                                                        NH                                 Ia1.170           NO.sub.2           CH.sub.3            C.sub.2                                                 H.sub.5       NH                           Ia1.171           NO.sub.2           CH.sub.3            CH.sub.2                                                --C.tbd.CH NH                              Ia1.172           NO.sub.2           C.sub.2 H.sub.5    CH.sub.3                                                        NH                                  Ia1.173           NO.sub.2           C.sub.2 H.sub.5    C.sub.2 H.sub.5                                                NH                                   Ia1.174           NO.sub.2           C.sub.2 H.sub.5    CH.sub.2                                                 --C.tbd.CH NH                              Ia1.175           NO.sub.2           OCH.sub.3           CH.sub.3                                                        NH                                 Ia1.176           NO.sub.2           OCH.sub.3           C.sub.2                                                 H.sub.5       NH                           Ia1.177           NO.sub.2           OCH.sub.3           CH.sub.2                                                --C.tbd.CH NH                              Ia1.178           NO.sub.2           OC.sub.2 H.sub.5   CH.sub.3                                                        NH                                  Ia1.179           NO.sub.2           OC.sub.2 H.sub.5   C.sub.2 H.sub.5                                                NH                                   Ia1.180           NO.sub.2           OC.sub.2 H.sub.5   CH.sub.2                                                 --C.tbd.CH NH                            ______________________________________                                    

In addition, the following 4-benzoyl-pyrazoles of the formula I areparticularly extraordinarily preferred:

the compounds Ia2, in particular the compounds Ia2.001-Ia2.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl: ##STR5## the compounds Ia3, in particular the compoundsIa3.001-Ia3.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl: ##STR6## the compoundsIa4, in particular the compounds Ia4.001-Ia4.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl:##STR7## the compounds Ia5, in particular the compounds Ia5.001-Ia5.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is iso-butyl: ##STR8## the compounds Ia6, in particularthe compounds Ia6.001-Ia6.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is methyl: ##STR9## thecompounds Ia7, in particular the compounds Ia7.001-Ia7.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isethyl and R¹² is methyl: ##STR10## the compounds Ia8, in particular thecompounds Ia8.001-Ia8.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² is methyl:##STR11## the compounds Ia9, in particular the compoundsIa9.001-Ia9.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² is methyl:##STR12## the compounds Ia10, in particular the compoundsIa10.001-Ia10.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² is methyl:##STR13## the compounds Ia11, in particular the compoundsIa11.001-Ia11.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is ethyl: ##STR14## the compoundsIa12, in particular the compounds Ia12.001-Ia12.180, which differ fromthe corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ and R¹²are ethyl: ##STR15## the compounds Ia13, in particular the compoundsIa13.001-Ia13.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is propyl and R¹² is ethyl:##STR16## the compounds Ia14, in particular the compoundsIa14.001-Ia14.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² is ethyl:##STR17## the compounds Ia15, in particular the compoundsIa15.001-Ia15.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² is ethyl:##STR18## the compounds Ia16, in particular the compoundsIa16.001-Ia16.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is n-propyl: ##STR19## thecompounds Ia17, in particular the compounds Ia17.001-Ia17.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl and R¹² is n-propyl: ##STR20## the compounds Ia18, inparticular the compounds Ia18.001-Ia18.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ and R¹² aren-propyl: ##STR21## the compounds Ia19, in particular the compoundsIa19.001-Ia19.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² is n-propyl:##STR22## the compounds Ia20, in particular the compoundsIa20.001-Ia20.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² is n-propyl:##STR23## the compounds Ia21, in particular the compoundsIa21.001-Ia21.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is iso-propyl: ##STR24## thecompounds Ia22, in particular the compounds Ia22.001-Ia22.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl and R¹² is iso-propyl: ##STR25## the compounds Ia23, inparticular the compounds Ia23.001-Ia23.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyland R¹² is iso-propyl: ##STR26## the compounds Ia24, in particular thecompounds Ia24.001-Ia24.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isiso-propyl: ##STR27## the compounds Ia25, in particular the compoundsIa25.001-Ia25.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² is iso-propyl:##STR28## the compounds Ia26, in particular the compoundsIa26.001-Ia26.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is n-butyl: ##STR29## the compoundsIa27, in particular the compounds Ia27.001-Ia27.180, which differ fromthe corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isethyl and R¹² is n-butyl: ##STR30## the compounds Ia28, in particularthe compounds Ia28.001-Ia28.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² isn-butyl: ##STR31## the compounds Ia29, in particular the compoundsIa29.001-Ia29.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ and R¹² are n-butyl: ##STR32## thecompounds Ia30, in particular the compounds Ia30.001-Ia30.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is iso-butyl and R¹² is n-butyl: ##STR33## the compounds Ia31, inparticular the compounds Ia31.001-Ia31.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹² issec-butyl: ##STR34## the compounds Ia32, in particular the compoundsIa32.001-Ia32.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² is sec-butyl:##STR35## the compounds Ia33, in particular the compoundsIa33.001-Ia33.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² is sec-butyl:##STR36## the compounds Ia34, in particular the compoundsIa34.001-Ia34.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² is sec-butyl:##STR37## the compounds Ia35, in particular the compoundsIa35.001-Ia35.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² is sec-butyl:##STR38## the compounds Ia36, in particular the compoundsIa36.001-Ia36.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is iso-butyl: ##STR39## thecompounds Ia37, in particular the compounds Ia37.001-Ia37.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹² is is [sic] ethyl and R¹³ is iso-butyl: ##STR40## the compoundsIa38, in particular the compounds Ia38.001-Ia38.180, which differ fromthe corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl and R¹² is iso-butyl: ##STR41## the compounds Ia39, inparticular the compounds Ia39.001-Ia39.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyland R¹² is iso-butyl: ##STR42## the compounds Ia40, in particular thecompounds Ia40.001-Ia40.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ and R¹² are iso-butyl:##STR43## the compounds Ia41, in particular the compoundsIa41.001-Ia41.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is methylcarbonyl: ##STR44## thecompounds Ia42, in particular the compounds Ia42.001-Ia42.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl and R¹² is methylcarbonyl: ##STR45## the compounds Ia43, inparticular the compounds Ia43.001-Ia43.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is propyland R¹² is methylcarbonyl: ##STR46## the compounds Ia44, in particularthe compounds Ia44.001-Ia44.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² ismethylcarbonyl: ##STR47## the compounds Ia45, in particular thecompounds Ia45.001-Ia45.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² ismethylcarbonyl: ##STR48## the compounds Ia46, in particular thecompounds Ia46.001-Ia46.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is ethylcarbonyl:##STR49## the compounds Ia47, in particular the compoundsIa47.001-Ia47.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² is ethylcarbonyl:##STR50## the compounds Ia48, in particular the compoundsIa48.001-Ia48.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is propyl and R¹² is ethylcarbonyl:##STR51## the compounds Ia49, in particular the compoundsIa49.001-Ia49.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isethylcarbonyl: ##STR52## the compounds Ia50, in particular the compoundsIa50.001-Ia50.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² isethylcarbonyl: ##STR53## the compounds Ia51, in particular the compoundsIa51.001-Ia51.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is n-propylcarbonyl: ##STR54## thecompounds Ia52, in particular the compounds Ia52.001-Ia52.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl and R¹² is n-propylcarbonyl: ##STR55## the compounds Ia53,in particular the compounds Ia53.001-Ia53.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is propyland R¹² is n-propylcarbonyl: ##STR56## the compounds Ia54, in particularthe compounds Ia54.001-Ia54.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isn-propylcarbonyl: ##STR57## the compounds Ia55, in particular thecompounds Ia55.001-Ia55.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² isn-propylcarbonyl: ##STR58## the compounds Ia56, in particular thecompounds Ia56.001-Ia56.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² istrifluoromethylcarbonyl: ##STR59## the compounds Ia57, in particular thecompounds Ia57.001-Ia57.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² istrifluoromethylcarbonyl: ##STR60## the compounds Ia58, in particular thecompounds Ia58.001-Ia58.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² istrifluoromethylcarbonyl: ##STR61## the compounds Ia59, in particular thecompounds Ia59.001-Ia59.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² istrifluoromethylcarbonyl: ##STR62## the compounds Ia60, in particular thecompounds Ia60.001-Ia60.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² istrifluoromethylcarbonyl: ##STR63## the compounds Ia61, in particular thecompounds Ia61.001-Ia61.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is methylsulfonyl:##STR64## the compounds Ia62, in particular the compoundsIa62.001-Ia62.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² is methylsulfonyl:##STR65## the compounds Ia63, in particular the compoundsIa63.001-Ia63.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² ismethylsulfonyl: ##STR66## the compounds Ia64, in particular thecompounds Ia64.001-Ia64.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² ismethylsulfonyl: ##STR67## the compounds Ia65, in particular thecompounds Ia65.001-Ia65.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² ismethylsulfonyl: ##STR68## the compounds Ia66, in particular thecompounds Ia66.001-Ia66.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is ethylsulfonyl:##STR69## the compounds Ia67, in particular the compoundsIa67.001-Ia67.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² is ethylsulfonyl:##STR70## the compounds Ia68, in particular the compoundsIa68.001-Ia68.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is propyl and R¹² is ethylsulfonyl:##STR71## the compounds Ia69, in particular the compoundsIa69.001-Ia69.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isethylsulfonyl: ##STR72## the compounds Ia70, in particular the compoundsIa70.001-Ia70.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² isethylsulfonyl: ##STR73## the compounds Ia71, in particular the compoundsIa71.001-Ia71.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is n-propylsulfonyl: ##STR74## thecompounds Ia72, in particular the compounds Ia72.001-Ia72.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl and R¹² is n-propylsulfonyl: ##STR75## the compounds Ia73,in particular the compounds Ia73.001-Ia73.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyland R¹² is n-propylsulfonyl: ##STR76## the compounds Ia74, in particularthe compounds Ia74.001-Ia74.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isn-propylsulfonyl: ##STR77## the compounds Ia75, in particular thecompounds Ia75.001-Ia75.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² isn-propylsulfonyl: ##STR78## the compounds Ia76, in particular thecompounds Ia76.001-Ia76.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is iso-propylsulfonyl:##STR79## the compounds Ia77, in particular the compoundsIa77.001-Ia77.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² isiso-propylsulfonyl: ##STR80## the compounds Ia78, in particular thecompounds Ia78.001-Ia78.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is propyl and R¹² isiso-propylsulfonyl: ##STR81## the compounds Ia79, in particular thecompounds Ia79.001-Ia79.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isiso-propylsulfonyl: ##STR82## the compounds Ia80, in particular thecompounds Ia80.001-Ia80.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² isiso-propylsulfonyl: ##STR83## the compounds Ia81, in particular thecompounds Ia81.001-Ia81.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is n-butylsulfonyl:##STR84## the compounds Ia82, in particular the compoundsIa82.001-Ia82.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² isn-butylsulfonyl: ##STR85## the compounds Ia83, in particular thecompounds Ia83.001-Ia83.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² isn-butylsulfonyl: ##STR86## the compounds Ia84, in particular thecompounds Ia84.001-Ia84.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isn-butylsulfonyl: ##STR87## the compounds Ia85, in particular thecompounds Ia85.001-Ia85.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² isn-butylsulfonyl: ##STR88## the compounds Ia86, in particular thecompounds Ia86.001-Ia86.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is iso-butylsulfonyl:##STR89## the compounds Ia87, in particular the compoundsIa87.001-Ia87.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² isiso-butylsulfonyl: ##STR90## the compounds Ia88, in particular thecompounds Ia88.001-Ia88.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² isiso-butylsulfonyl: ##STR91## the compounds Ia89, in particular thecompounds Ia89.001-Ia89.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isiso-butylsulfonyl: ##STR92## the compounds Ia90, in particular thecompounds Ia90.001-Ia90.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² isiso-butylsulfonyl: ##STR93## the compounds Ia91, in particular thecompounds Ia91.001-Ia91.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is sec-butylsulfonyl:##STR94## the compounds Ia92, in particular the compoundsIa92.001-Ia92.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² issec-butylsulfonyl: ##STR95## the compounds Ia93, in particular thecompounds Ia93.001-Ia93.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² issec-butylsulfonyl: ##STR96## the compounds Ia94, in particular thecompounds Ia94.001-Ia94.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² issec-butylsulfonyl: ##STR97## the compounds Ia95, in particular thecompounds Ia95.001-Ia95.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² issec-butylsulfonyl: ##STR98## the compounds Ia96, in particular thecompounds Ia96.001-Ia96.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² istrifluoromethylsulfonyl: ##STR99## the compounds Ia97, in particular thecompounds Ia97.001-Ia97.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² istrifluoromethylsulfonyl: ##STR100## the compounds Ia98, in particularthe compounds Ia98.001-Ia98.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² istrifluoromethylsulfonyl: ##STR101## the compounds Ia99, in particularthe compounds Ia99.001-Ia99.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² istrifluoromethylsulfonyl: ##STR102## the compounds Ia100, in particularthe compounds Ia100.001-Ia100.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² istrifluoromethylsulfonyl: ##STR103## the compounds Ia101, in particularthe compounds Ia101.001-Ia101.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is phenylcarbonylmethyl:##STR104## the compounds Ia102, in particular the compoundsIa102.001-Ia102.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² isphenylcarbonylmethyl: ##STR105## the compounds Ia103, in particular thecompounds Ia103.001-Ia103.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² isphenylcarbonylmethyl: ##STR106## the compounds Ia104, in particular thecompounds Ia104.001-Ia104.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isphenylcarbonylmethyl: ##STR107## the compounds Ia105, in particular thecompounds Ia105.001-Ia105.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² isphenylcarbonylmethyl: ##STR108## the compounds Ia106, in particular thecompounds Ia106.001-Ia106.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is phenylsulfonyl:##STR109## the compounds Ia107, in particular the compoundsIa107.001-Ia107.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² is phenylsulfonyl:##STR110## the compounds Ia108, in particular the compoundsIa108.001-Ia108.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² isphenylsulfonyl: ##STR111## the compounds Ia109, in particular thecompounds Ia109.001-Ia109.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² isphenylsulfonyl: ##STR112## the compounds Ia110, in particular thecompounds Ia110.001-Ia110.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² isphenylsulfonyl: ##STR113## the compounds Ia111, in particular thecompounds Ia111.001-Ia111.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is4-methylphenylsulfonyl: ##STR114## the compounds Ia112, in particularthe compounds Ia112.001-Ia112.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹² is4-methylphenylsulfonyl: ##STR115## the compounds Ia113, in particularthe compounds Ia113.001-Ia113.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹² is4-methylphenylsulfonyl: ##STR116## the compounds Ia114, in particularthe compounds Ia114.001-Ia114.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹² is4-methylphenylsulfonyl: ##STR117## the compounds Ia115, in particularthe compounds Ia115.001-Ia115.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹² is4-methylphenylsulfonyl: ##STR118## the compounds Ia116, in particularthe compounds Ia116.001-Ia116.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro: ##STR119## thecompounds Ia117, in particular the compounds Ia117.001-Ia117.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro and R¹¹ is ethyl: ##STR120## the compounds Ia118, inparticular the compounds Ia118.001-Ia118.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro andR¹¹ is propyl: ##STR121## the compounds Ia119, in particular thecompounds Ia119.001-Ia119.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro and R¹¹ isn-butyl: ##STR122## the compounds Ia120, in particular the compoundsIa120.001-Ia120.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹¹ is iso-butyl:##STR123## the compounds Ia121, in particular the compoundsIa121.001-Ia121.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹² is methyl:##STR124## the compounds Ia122, in particular the compoundsIa122.001-Ia122.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl and R¹² ismethyl: ##STR125## the compounds Ia123, in particular the compoundsIa123.001-Ia123.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl and R¹² ismethyl: ##STR126## the compounds Ia124, in particular the compoundsIa124.001-Ia124.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl and R¹² ismethyl: ##STR127## the compounds Ia125, in particular the compoundsIa125.001-Ia125.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl and R¹²is methyl: ##STR128## the compounds Ia126, in particular the compoundsIa126.001-Ia126.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹² is ethyl:##STR129## the compounds Ia127, in particular the compoundsIa127.001-Ia127.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹¹ and R¹² are ethyl:##STR130## the compounds Ia128, in particular the compoundsIa128.001-Ia128.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl and R¹² isethyl: ##STR131## the compounds Ia129, in particular the compoundsIa129.001-Ia129.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl and R¹² isethyl: ##STR132## the compounds Ia130, in particular the compoundsIa130.001-Ia130.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl and R¹²is ethyl: ##STR133## the compounds Ia131, in particular the compoundsIa131.001-Ia131.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹² is n-propyl:##STR134## the compounds Ia132, in particular the compoundsIa132.001-Ia132.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl and R¹² isn-propyl: ##STR135## the compounds Ia133, in particular the compoundsIa133.001-Ia133.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is is [sic] nitro and R¹¹ and R¹²are n-propyl: ##STR136## the compounds Ia134, in particular thecompounds Ia134.001-Ia134.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyland R¹² is n-propyl: ##STR137## the compounds Ia135, in particular thecompounds Ia135.001-Ia135.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyland R¹² is n-propyl: ##STR138## the compounds Ia136, in particular thecompounds Ia136.001-Ia136.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro and R¹² isiso-propyl: ##STR139## the compounds Ia137, in particular the compoundsIa137.001-Ia137.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl and R¹² isiso-propyl: ##STR140## the compounds Ia138, in particular the compoundsIa138.001-Ia318.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl and R¹² isiso-propyl: ##STR141## the compounds Ia139, in particular the compoundsIa139.001-Ia139.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl and R¹² isiso-propyl: ##STR142## the compounds Ia140, in particular the compoundsIa140.001-Ia140.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl and R¹²is iso-propyl: ##STR143## the compounds Ia141, in particular thecompounds Ia141.001-Ia141.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro and R¹² isn-butyl: ##STR144## the compounds Ia142, in particular the compoundsIa142.001-Ia142.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl and R¹² isn-butyl: ##STR145## the compounds Ia143, in particular the compoundsIa143.001-Ia143.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl and R¹² isn-butyl: ##STR146## the compounds Ia144, in particular the compoundsIa144.001-Ia144.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹¹ and R¹² aren-butyl: ##STR147## the compounds Ia145, in particular the compoundsIa145.001-Ia145.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl and R¹²is n-butyl: ##STR148## the compounds Ia146, in particular the compoundsIa146.001-Ia146.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹² is sec-butyl:##STR149## the compounds Ia147, in particular the compoundsIa147.001-Ia147.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl and R¹² issec-butyl: ##STR150## the compounds Ia148, in particular the compoundsIa148.001-Ia148.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl and R¹² issec-butyl: ##STR151## the compounds Ia149, in particular the compoundsIa149.001-Ia149.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl and R¹² issec-butyl: ##STR152## the compounds Ia150, in particular the compoundsIa150.001-Ia150.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl and R¹²is sec-butyl: ##STR153## the compounds Ia11, in particular the compoundsIa151.001-Ia151.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹² is iso-butyl:##STR154## the compounds Ia152, in particular the compoundsIa152.001-Ia152.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl and R¹² isiso-butyl: ##STR155## the compounds Ia153, in particular the compoundsIa153.001-Ia153.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl and R¹² isiso-butyl: ##STR156## the compounds Ia154, in particular the compoundsIa154.001-Ia154.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl and R¹² isiso-butyl: ##STR157## the compounds Ia155, in particular the compoundsIa155.001-Ia154.180 [sic], which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹¹ and R¹² areiso-butyl: ##STR158## the compounds Ia156, in particular the compoundsIa156.001-Ia156.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro and R¹² is methylcarbonyl:##STR159## the compounds Ia157, in particular the compoundsIa157.001-Ia157.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl and R¹² ismethylcarbonyl: ##STR160## the compounds Ia158, in particular thecompounds Ia158.001-Ia158.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyland R¹² is methylcarbonyl: ##STR161## the compounds Ia159, in particularthe compounds Ia159.001-Ia159.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyland R¹² is methylcarbonyl: ##STR162## the compounds Ia160, in particularthe compounds Ia160.001-Ia160.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyland R¹² is methylcarbonyl: ##STR163## the compounds Ia161, in particularthe compounds Ia161.001-Ia160.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro and R¹² isethylcarbonyl: ##STR164## the compounds Ia162, in particular thecompounds Ia162.001-Ia162.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl andR¹² is ethylcarbonyl: ##STR165## the compounds Ia163, in particular thecompounds Ia163.001-Ia163.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyland R¹² is ethylcarbonyl: ##STR166## the compounds Ia164, in particularthe compounds Ia164.001-Ia164.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyland R¹² is ethylcarbonyl: ##STR167## the compounds Ia165, in particularthe compounds Ia165.001-Ia165.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyland R¹² is ethylcarbonyl: ##STR168## the compounds Ia166, in particularthe compounds Ia166.001-Ia166.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro and R¹² isn-propylcarbonyl: ##STR169## the compounds Ia167, in particular thecompounds Ia167.001-Ia167.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl andR¹² is n-propylcarbonyl: ##STR170## the compounds Ia168, in particularthe compounds Ia168.001-Ia168.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyland R¹² is n-propylcarbonyl: ##STR171## the compounds Ia169, inparticular the compounds Ia169.001-Ia169.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-butyl and R¹² is n-propylcarbonyl: ##STR172## the compoundsIa170, in particular the compounds Ia170.001-Ia170.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is iso-butyl and R¹² is n-propylcarbonyl: ##STR173## thecompounds Ia171, in particular the compounds Ia171.001-Ia171.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro and R¹² is trifluoromethylcarbonyl: ##STR174## the compoundsIa172, in particular the compounds Ia172.001-Ia172.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl and R¹² is trifluoromethylcarbonyl: ##STR175## thecompounds Ia173, in particular the compounds Ia173.001-Ia173.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-propyl and R¹² is trifluoromethylcarbonyl:##STR176## the compounds Ia174, in particular the compoundsIa174.001-Ia174.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl and R¹² istrilfuoromethylcarbonyl [sic]: ##STR177## the compounds Ia175, inparticular the compounds Ia175.001-Ia175.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is iso-butyl and R¹² is trifluoromethylcarbonyl: ##STR178## thecompounds Ia176, in particular the compounds Ia176.001-Ia176.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro and R¹² is methylsulfonyl: ##STR179## the compounds Ia177,in particular the compounds Ia177.001-Ia177.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is ethyl and R¹² is methylsulfonyl: ##STR180## the compounds Ia178,in particular the compounds Ia178.001-Ia178.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl and R¹² is methylsulfonyl: ##STR181## the compoundsIa179, in particular the compounds Ia179.001-Ia179.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-butyl and R¹² is methylsulfonyl: ##STR182## thecompounds Ia180, in particular the compounds Ia180.001-Ia180.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is iso-butyl and R¹² is methylsulfonyl: ##STR183## thecompounds Ia181, in particular the compounds Ia181.001-Ia181.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro and R¹² is ethylsulfonyl: ##STR184## the compounds Ia182, inparticular the compounds Ia182.001-Ia182.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is ethyl and R¹² is ethylsulfonyl: ##STR185## the compounds Ia183,in particular the compounds Ia183.001-Ia183.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl and R¹² is ethylsulfonyl: ##STR186## the compoundsIa184, in particular the compounds Ia184.001-Ia184.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-butyl and R¹² is ethylsulfonyl: ##STR187## the compoundsIa185, in particular the compounds Ia185.001-Ia185.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is iso-butyl and R¹² is ethylsulfonyl: ##STR188## thecompounds Ia186, in particular the compounds Ia186.001-Ia186.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro and R¹² is n-propylsulfonyl: ##STR189## the compounds Ia187,in particular the compounds Ia187.001-Ia187.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is ethyl and R¹² is n-propylsulfonyl: ##STR190## the compoundsIa188, in particular the compounds Ia188.001-Ia188.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-propyl and R¹² is n-propylsulfonyl: ##STR191## thecompounds Ia189, in particular the compounds Ia189.001-Ia189.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-butyl and R¹² is n-propylsulfonyl: ##STR192## thecompounds Ia190, in particular the compounds Ia190.001-Ia190.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is iso-butyl and R¹² is n-propylsulfonyl: ##STR193##the compounds Ia191, in particular the compounds Ia191.001-Ia191.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro and R¹² is iso-propylsulfonyl: ##STR194## thecompounds Ia192, in particular the compounds Ia192.001-Ia192.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is ethyl and R¹² is iso-propylsulfonyl: ##STR195## thecompounds Ia193, in particular the compounds Ia193.001-Ia193.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-propyl and R¹² is iso-propylsulfonyl: ##STR196##the compounds Ia194, in particular the compounds Ia194.001-Ia194.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is n-butyl and R¹² is iso-propylsulfonyl:##STR197## the compounds Ia195, in particular the compoundsIa195.001-Ia195.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl and R¹²is iso-propylsulfonyl: ##STR198## the compounds Ia196, in particular thecompounds Ia196.001-Ia196.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro and R¹² isn-butylsulfonyl: ##STR199## the compounds Ia197, in particular thecompounds Ia197.001-Ia197.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl andR¹² is n-butylsulfonyl: ##STR200## the compounds Ia198, in particularthe compounds Ia198.001-Ia198.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyland R¹² is n-butylsulfonyl: ##STR201## the compounds Ia199, inparticular the compounds Ia199.001-Ia199.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-butyl and R¹² is n-butylsulfonyl: ##STR202## the compoundsIa200, in particular the compounds Ia200.001-Ia200.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is iso-butyl and R¹² is n-butylsulfonyl: ##STR203## thecompounds Ia201, in particular the compounds Ia201.001-Ia201.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro and R¹² is iso-butylsulfonyl: ##STR204## the compoundsIa202, in particular the compounds Ia202.001-Ia202.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl and R¹² is iso-butylsulfonyl: ##STR205## thecompounds Ia203, in particular the compounds Ia203.001-Ia203.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-propyl and R¹² is iso-butylsulfonyl: ##STR206##the compounds Ia204, in particular the compounds Ia204.001-Ia204.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is n-butyl and R¹² is iso-butylsulfonyl:##STR207## the compounds Ia205, in particular the compoundsIa205.001-Ia205.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl and R¹²is iso-butylsulfonyl: ##STR208## the compounds Ia206, in particular thecompounds Ia206.001-Ia2066.180 [sic], which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro andR¹² is sec-butylsulfonyl: ##STR209## the compounds Ia207, in particularthe compounds Ia207.001-Ia207.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl andR¹² is sec-butylsulfonyl: ##STR210## the compounds Ia208, in particularthe compounds Ia208.001-Ia208.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyland R¹² is sec-butylsulfonyl: ##STR211## the compounds Ia209, inparticular the compounds Ia209.001-Ia209.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-butyl and R¹² is sec-butylsulfonyl: ##STR212## the compoundsIa210, in particular the compounds Ia210.001-Ia210.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is iso-butyl and R¹² is sec-butylsulfonyl: ##STR213## thecompounds Ia211, in particular the compounds Ia211.001-Ia211.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro and R¹² is trifluoromethylsulfonyl: ##STR214## the compoundsIa212, in particular the compounds Ia212.001-Ia212.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl and R¹² is trifluoromethylsulfonyl: ##STR215## thecompounds Ia213, in particular the compounds Ia213.001-Ia213.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-propyl and R¹² is trifluoromethylsulfonyl:##STR216## the compounds Ia214, in particular the compoundsIa214.001-Ia214.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl and R¹² istrifluoromethylsulfonyl: ##STR217## the compounds Ia215, in particularthe compounds Ia215.001-Ia125.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyland R¹² is trifluoromethylsulfonyl: ##STR218## the compounds Ia216, inparticular the compounds Ia216.001-Ia216.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is methyl and R¹² is phenylcarbonylmethyl: ##STR219## the compoundsIa217, in particular the compounds Ia217.001-Ia217.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl and R¹² is phenylcarbonylmethyl: ##STR220## thecompounds Ia218, in particular the compounds Ia218.001-Ia218.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-propyl and R¹² is phenylcarbonylmethyl: ##STR221##the compounds Ia219, in particular the compounds Ia219.001-Ia219.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is n-butyl and R¹² is phenylcarbonylmethyl:##STR222## the compounds Ia220, in particular the compoundsIa220.001-Ia220.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl and R¹²is phenylcarbonylmethyl: ##STR223## the compounds Ia221, in particularthe compounds Ia221.001-Ia221.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro and R¹² isphenylsulfonyl: ##STR224## the compounds Ia222, in particular thecompounds Ia222.001-Ia222.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl andR¹² is phenylsulfonyl: ##STR225## the compounds Ia223, in particular thecompounds Ia223.001-Ia223.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyland R¹² is phenylsulfonyl: ##STR226## the compounds Ia224, in particularthe compounds Ia224.001-Ia224.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyland R¹² is phenylsulfonyl: ##STR227## the compounds Ia225, in particularthe compounds Ia225.001-Ia225.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyland R¹² is phenylsulfonyl: ##STR228## the compounds Ia226, in particularthe compounds Ia226.001-Ia226.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro and R¹² is4-methylphenylsulfonyl: ##STR229## the compounds Ia227, in particularthe compounds Ia227.001-Ia227.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl andR¹² is 4-methylphenylsulfonyl: ##STR230## the compounds Ia228, inparticular the compounds Ia228.001-Ia228.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl and R¹² is 4-methylphenylsulfonyl: ##STR231## thecompounds Ia229, in particular the compounds Ia229.001-Ia229.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-butyl and R¹² is 4-methylphenylsulfonyl:##STR232## the compounds Ia230, in particular the compoundsIa230.001-Ia230.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl and R¹²is 4-methylphenylsulfonyl: ##STR233## the compounds Ia231, in particularthe compounds Ia231.001-Ia231.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl:##STR234## the compounds Ia232, in particular the compoundsIa232.001-Ia232.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹¹ is ethyl:##STR235## the compounds Ia233, in particular the compoundsIa233.001-Ia233.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹¹ isn-propyl: ##STR236## the compounds Ia234, in particular the compoundsIa234.001-Ia234.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹¹ isn-butyl: ##STR237## the compounds Ia235, in particular the compoundsIa235.001-Ia235.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹¹ isiso-butyl: ##STR238## the compounds Ia236, in particular the compoundsIa236.001-Ia236.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹² is methyl:##STR239## the compounds Ia237, in particular the compoundsIa237.001-Ia237.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is ethyl andR¹² is methyl: ##STR240## the compounds Ia238, in particular thecompounds Ia238.001-Ia238.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-propyl and R¹² is methyl: ##STR241## the compounds Ia239, inparticular the compounds Ia239.001-Ia239.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl and R¹² is methyl: ##STR242## thecompounds Ia240, in particular the compounds Ia240.001-Ia240.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is iso-butyl and R¹² is methyl: ##STR243## thecompounds Ia241, in particular the compounds Ia241.001-Ia241.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl and R¹² is ethyl: ##STR244## the compounds Ia242,in particular the compounds Ia242.001-Ia242.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl and R¹¹ and R¹² is ethyl: ##STR245## the compounds Ia243,in particular the compounds Ia243.001-Ia243.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl and R¹² is ethyl: ##STR246## thecompounds Ia244, in particular the compounds Ia244.001-Ia244.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl and R¹² is ethyl: ##STR247## thecompounds Ia245, in particular the compounds Ia245.001-Ia245.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is iso-butyl and R¹² is ethyl: ##STR248## thecompounds Ia246, in particular the compounds Ia246.001-Ia246.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl and R¹² is n-propyl: ##STR249## the compoundsIa247, in particular the compounds Ia247.001-Ia247.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl R¹¹ is ethyl and R¹² is n-propyl: ##STR250## thecompounds Ia248, in particular the compounds Ia248.001-Ia248.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl and R¹¹ and R¹² are n-propyl: ##STR251## thecompounds Ia249, in particular the compounds Ia249.001-Ia249.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl and R¹² is n-propyl: ##STR252## thecompounds Ia250, in particular the compounds Ia250.001-Ia250.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is iso-butyl and R¹² is n-propyl: ##STR253##the compounds Ia251, in particular the compounds Ia251.001-Ia251.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl and R¹² is iso-propyl: ##STR254## thecompounds Ia252, in particular the compounds Ia252.001-Ia252.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl and R¹² is iso-propyl: ##STR255## thecompounds Ia253, in particular the compounds Ia253.001-Ia253.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-propyl and R¹² is iso-propyl: ##STR256##the compounds Ia254, in particular the compounds Ia254.001-Ia254.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is n-butyl and R¹² is iso-propyl:##STR257## the compounds Ia255, in particular the compoundsIa255.001-Ia255.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyland R¹² is iso-propyl: ##STR258## the compounds Ia256, in particular thecompounds Ia256.001-Ia256.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹²is n-butyl: ##STR259## the compounds Ia257, in particular the compoundsIa257.001-Ia257.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is ethyl andR¹² is n-butyl: ##STR260## the compounds Ia258, in particular thecompounds Ia258.001-Ia258.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-propyl and R¹² is n-butyl: ##STR261## the compounds Ia259, inparticular the compounds Ia259.001-Ia259.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl and R¹¹ and R¹² are n-butyl: ##STR262## the compoundsIa260, in particular the compounds Ia260.001-Ia260.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl and R¹² is n-butyl: ##STR263## thecompounds Ia261, in particular the compounds Ia261.001-Ia261.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl and R¹² is sec-butyl: ##STR264## the compoundsIa262, in particular the compounds Ia262.001-Ia262.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is ethyl and R¹² is sec-butyl: ##STR265## thecompounds Ia263, in particular the compounds Ia263.001-Ia263.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-propyl and R¹² is sec-butyl: ##STR266##the compounds Ia264, in particular the compounds Ia264.001-Ia264.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is n-butyl and R¹² is sec-butyl:##STR267## the compounds Ia265, in particular the compoundsIa265.001-Ia265.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyland R¹² is sec-butyl: ##STR268## the compounds Ia266, in particular thecompounds Ia266.001-Ia266.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹²is iso-butyl: ##STR269## the compounds Ia267, in particular thecompounds Ia267.001-Ia267.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl and R¹² is iso-butyl: ##STR270## the compounds Ia268, inparticular the compounds Ia268.001-Ia268.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl and R¹² is iso-butyl: ##STR271## thecompounds Ia269, in particular the compounds Ia269.001-Ia269.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl and R¹² is iso-butyl: ##STR272##the compounds Ia270, in particular the compounds Ia270.001-Ia270.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl and R¹¹ and R¹² are iso-butyl: ##STR273##the compounds Ia271, in particular the compounds Ia271.001-Ia271.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl and R¹² is methylcarbonyl: ##STR274## thecompounds Ia272, in particular the compounds Ia272.001-Ia272.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl and R¹² is methylcarbonyl: ##STR275##the compounds Ia273, in particular the compounds Ia273.001-Ia273.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is n-propyl and R¹² ismethylcarbonyl: ##STR276## the compounds Ia274, in particular thecompounds Ia274.001-Ia274.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-butyl and R¹² is methylcarbonyl: ##STR277## the compounds Ia275, inparticular the compounds Ia275.001-Ia275.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl and R¹² is methylcarbonyl: ##STR278##the compounds Ia276, in particular the compounds Ia276.001-Ia276.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl and R¹² is ethylcarbonyl: ##STR279## thecompounds Ia277, in particular the compounds Ia277.001-Ia277.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl and R¹² is ethylcarbonyl: ##STR280##the compounds Ia278, in particular the compounds Ia278.001-Ia278.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is n-propyl and R¹² isethylcarbonyl: ##STR281## the compounds Ia279, in particular thecompounds Ia279.001-Ia279.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-butyl and R¹² is ethylcarbonyl: ##STR282## the compounds Ia280, inparticular the compounds Ia280.001-Ia280.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl and R¹² is ethylcarbonyl: ##STR283##the compounds Ia281, in particular the compounds Ia281.001-Ia281.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl and R¹² is n-propylcarbonyl: ##STR284##the compounds Ia282, in particular the compounds Ia282.001-Ia282.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is ethyl and R¹² isn-propylcarbonyl: ##STR285## the compounds Ia283, in particular thecompounds Ia283.001-Ia283.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-propyl and R¹² is n-propylcarbonyl: ##STR286## the compounds Ia284, inparticular the compounds Ia284.001-Ia284.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl and R¹² is n-propylcarbonyl: ##STR287##the compounds Ia285, in particular the compounds Ia285.001-Ia285.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is iso-butyl and R¹² isn-propylcarbonyl: ##STR288## the compounds Ia286, in particular thecompounds Ia286.001-Ia286.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹¹is trifluoromethylcarbonyl: ##STR289## the compounds Ia287, inparticular the compounds Ia287.001-Ia287.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is ethyl and R¹² is trifluoromethylcarbonyl:##STR290## the compounds Ia288, in particular the compoundsIa288.001-Ia288.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyland R¹² is trifluoromethylcarbonyl: ##STR291## the compounds Ia289, inparticular the compounds Ia289.001-Ia289.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl and R¹² is trifluoromethylcarbonyl:##STR292## the compounds Ia290, in particular the compoundsIa290.001-Ia290.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyland R¹² is trifluoromethylcarbonyl: ##STR293## the compounds Ia291, inparticular the compounds Ia291.001-Ia291.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ and R¹² aremethylsulfonyl: ##STR294## the compounds Ia292, in particular thecompounds Ia292.001-Ia292.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ and R¹² are methylsulfonyland R¹¹ is ethyl: ##STR295## the compounds Ia293, in particular thecompounds Ia293.001-Ia293.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ and R¹² are methylsulfonyland R¹¹ is n-propyl: ##STR296## the compounds Ia294, in particular thecompounds Ia294.001-Ia294.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ and R¹² are methylsulfonyland R¹¹ is n-butyl: ##STR297## the compounds Ia295, in particular thecompounds Ia295.001-Ia295.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ and R¹² are methylsulfonyland R¹¹ is iso-butyl: ##STR298## the compounds Ia296, in particular thecompounds Ia296.001-Ia296.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹²is ethylsulfonyl: ##STR299## the compounds Ia297, in particular thecompounds Ia297.001-Ia297.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl and R¹² is ethylsulfonyl: ##STR300## the compounds Ia298, inparticular the compounds Ia298.001-Ia298.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl and R¹² is ethylsulfonyl: ##STR301## thecompounds Ia299, in particular the compounds Ia299.001-Ia299.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl and R¹² is ethylsulfonyl:##STR302## the compounds Ia300, in particular the compoundsIa300.001-Ia300.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyland R¹² is ethylsulfonyl: ##STR303## the compounds Ia301, in particularthe compounds Ia301.001-Ia301.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹²is n-propylsulfonyl: ##STR304## the compounds Ia302, in particular thecompounds Ia302.001-Ia302.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl and R¹² is n-propylsulfonyl: ##STR305## the compounds Ia303, inparticular the compounds Ia303.001-Ia303.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl and R¹² is n-propylsulfonyl: ##STR306##the compounds Ia304, in particular the compounds Ia304.001-Ia304.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is n-butyl and R¹² isn-propylsulfonyl: ##STR307## the compounds Ia305, in particular thecompounds Ia305.001-Ia305.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isiso-butyl and R¹² is n-propylsulfonyl: ##STR308## the compounds Ia306,in particular the compounds Ia306.001-Ia306.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl and R¹² is iso-propylsulfonyl: ##STR309## the compoundsIa307, in particular the compounds Ia307.001-Ia307.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is ethyl and R¹² is iso-propylsulfonyl: ##STR310##the compounds Ia308, in particular the compounds Ia308.001-Ia308.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is n-propyl and R¹² isiso-propylsulfonyl: ##STR311## the compounds Ia309, in particular thecompounds Ia309.001-Ia309.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-butyl and R¹² is iso-propylsulfonyl: ##STR312## the compounds Ia310,in particular the compounds Ia310.001-Ia310.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl and R¹² is iso-propylsulfonyl:##STR313## the compounds Ia311, in particular the compoundsIa311.001-Ia311.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹² isn-butylsulfonyl: ##STR314## the compounds Ia312.001-Ia312.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl and R¹² is n-butylsulfonyl:##STR315## the compounds Ia313, in particular the compoundsIa313.001-Ia313.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyland R¹² is n-butylsulfonyl: ##STR316## the compounds Ia314, inparticular the compounds Ia314.001-Ia314.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl and R¹² is n-butylsulfonyl: ##STR317##the compounds Ia315, in particular the compounds Ia315.001-Ia315.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is iso-butyl and R¹² isn-butylsulfonyl: ##STR318## the compounds Ia316, in particular thecompounds Ia316.001-Ia316.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹²is iso-butylsulfonyl: ##STR319## the compounds Ia317, in particular thecompounds Ia317.001-Ia317.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl and R¹² is iso-butylsulfonyl: ##STR320## the compounds Ia318, inparticular the compounds Ia318.001-Ia318.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl and R¹² is iso-butylsulfonyl: ##STR321##the compounds Ia319, in particular the compounds Ia319.001-Ia319.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is n-butyl and R¹² isiso-butylsulfonyl: ##STR322## the compounds Ia320, in particular thecompounds Ia320.001-Ia320.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isiso-butyl and R¹² is iso-butylsulfonyl: ##STR323## the compounds Ia321,in particular the compounds Ia321.001-Ia321.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl and R¹² is sec-butylsulfonyl: ##STR324## the compoundsIa322, in particular the compounds Ia322.001-Ia322.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is ethyl and R¹² is sec-butylsulfonyl: ##STR325##the compounds Ia323, in particular the compounds Ia323.001-Ia323.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is is [sic] n-propyl and R¹² issec-butylsulfonyl: ##STR326## the compounds Ia324, in particular thecompounds Ia324.001-Ia324.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-butyl and R¹² is sec-butylsulfonyl: ##STR327## the compounds Ia325, inparticular the compounds Ia325.001-Ia325.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl and R¹² is sec-butylsulfonyl:##STR328## the compounds Ia326, in particular the compoundsIa326.001-Ia326.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹² istrifluoromethylsulfonyl: ##STR329## the compounds Ia327, in particularthe compounds Ia327.001-Ia327.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl and R¹² is trifluoromethylsulfonyl: ##STR330## the compoundsIa328, in particular the compounds Ia328.001-Ia328.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl and R¹² is trifluoromethylsulfonyl:##STR331## the compounds Ia329, in particular the compoundsIa329.001-Ia329.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-butyland R¹² is trifluoromethylsulfonyl: ##STR332## the compounds Ia330, inparticular the compounds Ia330.001-Ia330.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl and R¹² is trifluoromethylsulfonyl:##STR333## the compounds Ia331, in particular the compoundsIa331.001-Ia331.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹² isphenylcarbonylmethyl: ##STR334## the compounds Ia332, in particular thecompounds Ia332.001-Ia332.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl and R¹² is phenylcarbonylmethyl: ##STR335## the compounds Ia333,in particular the compounds Ia333.001-Ia333.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl and R¹² is phenylcarbonylmethyl:##STR336## the compounds Ia334, in particular the compoundsIa334.001-Ia334.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-butyland R¹² is phenylcarbonylmethyl: ##STR337## the compounds Ia335, inparticular the compounds Ia335.001-Ia335.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl and R¹² is phenylcarbonylmethyl:##STR338## the compounds Ia336, in particular the compoundsIa336.001-Ia336.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl and R¹² isphenylsulfonyl: ##STR339## the compounds Ia337, in particular thecompounds Ia337.001-Ia337.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl and R¹² is phenylsulfonyl: ##STR340## the compounds Ia338, inparticular the compounds Ia338.001-Ia338.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl and R¹² is phenylsulfonyl: ##STR341##the compounds Ia339, in particular the compounds Ia339.001-Ia339.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is n-butyl and R¹² isphenylsulfonyl: ##STR342## the compounds Ia340, in particular thecompounds Ia340.001-Ia340.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isiso-butyl and R¹² is phenylsulfonyl: ##STR343## the compounds Ia341, inparticular the compounds Ia341.001-Ia341.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl and R¹² is 4-methylphenylsulfonyl: ##STR344## thecompounds Ia342, in particular the compounds Ia342.001-Ia342.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl and R¹² is 4-methylphenylsulfonyl:##STR345## the compounds Ia343, in particular the compoundsIa343.001-Ia343.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyland R¹² is 4-methylphenylsulfonyl: ##STR346## the compounds Ia344, inparticular the compounds Ia344.001-Ia344.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl and R¹² is 4-methylphenylsulfonyl:##STR347## the compounds Ia345, in particular the compoundsIa345.001-Ia345.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyland R¹² is 4-methylphenylsulfonyl: ##STR348## the compounds Ia346, inparticular the compounds Ia346.001-Ia346.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹³ is methyl:##STR349## the compounds Ia347, in particular the compoundsIa347.001-Ia347.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl and R¹³ is methyl:##STR350## the compounds Ia348, in particular the compoundsIa348.001-Ia348.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹³ is methyl:##STR351## the compounds Ia349, in particular the compoundsIa349.001-Ia349.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl and R¹³ is methyl:##STR352## the compounds Ia350, in particular the compoundsIa350.001-Ia350.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl and R¹³ is methyl:##STR353## the compounds Ia351, in particular the compoundsIa351.001-Ia351.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² and R¹³ are methyl: ##STR354## thecompounds Ia352, in particular the compounds Ia352.001-Ia352.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl and R¹² and R¹³ are methyl: ##STR355## the compounds Ia353,in particular the compounds Ia353.001-Ia353.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyland R¹² and R¹³ are methyl: ##STR356## the compounds Ia354, inparticular the compounds Ia354.001-Ia354.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyland R¹² and R¹³ are methyl: ##STR357## the compounds Ia355, inparticular the compounds Ia355.001-Ia355.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isiso-butyl and R¹² and R¹³ are methyl: ##STR358## the compounds Ia356, inparticular the compounds Ia356.001-Ia356.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹² is ethyland R¹³ is methyl: ##STR359## the compounds Ia357, in particular thecompounds Ia357.001-Ia357.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ and R¹² are ethyl and R¹³is methyl: ##STR360## the compounds Ia358, in particular the compoundsIa358.001-Ia358.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl, R¹² is ethyl and R¹³is methyl: ##STR361## the compounds Ia359, in particular the compoundsIa359.001-Ia359.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl, R¹² is ethyl and R¹³ ismethyl: ##STR362## the compounds Ia360, in particular the compoundsIa360.001-Ia360.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl, R¹² is ethyl and R¹³is methyl: ##STR363## the compounds Ia361, in particular the compoundsIa361.001-Ia361.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl and R¹³ is methyl:##STR364## the compounds Ia362, in particular the compoundsIa362.001-Ia362.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl, R¹² is n-propyl and R¹³is methyl: ##STR365## the compounds Ia363, in particular the compoundsIa363.001-Ia363.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ and R¹² are n-propyl and R¹³ ismethyl: ##STR366## the compounds Ia364, in particular the compoundsIa364.001-Ia364.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl, R¹² is n-propyl and R¹³is methyl: ##STR367## the compounds Ia365, in particular the compoundsIa365.001-Ia365.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl, R¹² is n-propyl andR¹³ is methyl: ##STR368## the compounds Ia366, in particular thecompounds Ia366.001-Ia366.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is iso-propyl and R¹³ ismethyl: ##STR369## the compounds Ia367, in particular the compoundsIa367.001-Ia367.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl, R¹² is iso-propyl and R¹³is methyl: ##STR370## the compounds Ia368, in particular the compoundsIa368.001-Ia368.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl, R¹² is iso-propyl andR¹³ is methyl: ##STR371## the compounds Ia369, in particular thecompounds Ia369.001-Ia369.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl, R¹² isiso-propyl and R¹³ is methyl: ##STR372## the compounds Ia370, inparticular the compounds Ia370.001-Ia370.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isiso-butyl, R¹² is iso-propyl and R¹³ is methyl: ##STR373## the compoundsIa371, in particular the compounds Ia371.001-Ia371.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹² isn-butyl and R¹³ is methyl: ##STR374## the compounds Ia372, in particularthe compounds Ia372.001-Ia372.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl, R¹² is n-butyland R¹³ is methyl: ##STR375## the compounds Ia373, in particular thecompounds Ia373.001-Ia373.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl, R¹² isn-butyl and R¹³ is methyl: ##STR376## the compounds Ia374, in particularthe compounds Ia374.001-Ia374.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ and R¹² are n-butyl andR¹³ is methyl: ##STR377## the compounds Ia375, in particular thecompounds Ia375.001-Ia375.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is iso-butyl, R¹² isn-butyl and R¹³ is methyl: ##STR378## the compounds Ia376, in particularthe compounds Ia376.001-Ia376.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is sec-butyl and R¹³ ismethyl: ##STR379## the compounds Ia377, in particular the compoundsIa377.001-Ia377.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl, R¹² is sec-butyl and R¹³is methyl: ##STR380## the compounds Ia378, in particular the compoundsIa378.001-Ia378.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-propyl, R¹² is sec-butyl andR¹³ is methyl: ##STR381## the compounds Ia379, in particular thecompounds Ia379.001-Ia379.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl, R¹² issec-butyl and R¹³ is methyl: ##STR382## the compounds Ia380, inparticular the compounds Ia380.001-Ia380.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isiso-butyl, R¹² is sec-butyl and R¹³ is methyl: ##STR383## the compoundsIa381, in particular the compounds Ia381.001-Ia381.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹² isiso-butyl and R¹³ is methyl: ##STR384## the compounds Ia382, inparticular the compounds Ia382.001-Ia382.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl,R¹² is iso-butyl and R¹³ is methyl: ##STR385## the compounds Ia383, inparticular the compounds Ia383.001-Ia383.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is iso-butyl and R¹³ is methyl: ##STR386## the compoundsIa384, in particular the compounds Ia384.001-Ia384.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-butyl, R¹² is iso-butyl and R¹³ is methyl: ##STR387## the compoundsIa385, in particular the compounds Ia385.001-Ia385.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹and R¹² are iso-butyl and R¹³ is methyl: ##STR388## the compounds Ia386,in particular the compounds Ia386.001-Ia386.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹² ismethylcarbonyl and R¹³ is methyl: ##STR389## the compounds Ia387, inparticular the compounds Ia387.001-Ia387.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl,R¹² is methylcarbonyl and R¹³ is methyl: ##STR390## the compounds Ia388,in particular the compounds Ia388.001-Ia388.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is methylcarbonyl and R¹³ is methyl: ##STR391## thecompounds Ia389, in particular the compounds Ia389.001-Ia389.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-butyl, R¹² is methylcarbonyl and R¹³ is methyl: ##STR392## thecompounds Ia390, in particular the compounds Ia390.001-Ia390.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is iso-butyl, R¹² is methylcarbonyl and R¹³ is methyl: ##STR393##the compounds Ia391, in particular the compounds Ia391.001-Ia391.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is ethylcarbonyl and R¹³ is methyl: ##STR394## thecompounds Ia392, in particular the compounds Ia392.001-Ia392.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl, R¹² is ethylcarbonyl and R¹³ is methyl: ##STR395## thecompounds Ia393, in particular the compounds Ia393.001-Ia393.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-propyl, R¹² is ethylcarbonyl and R¹³ is methyl: ##STR396## thecompounds Ia394, in particular the compounds Ia394.001-Ia394.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-butyl, R¹² is ethylcarbonyl and R¹³ is methyl: ##STR397## thecompounds Ia395, in particular the compounds Ia395.001-Ia395.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is iso-butyl, R¹² is ethylcarbonyl and R¹³ is methyl: ##STR398## thecompounds Ia396, in particular the compounds Ia396.001-Ia396.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹² is phenylsulfonyl and R¹³ is methyl: ##STR399## the compounds Ia397,in particular the compounds Ia397.001-Ia397.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl,R¹² is phenylsulfonyl and R¹³ is methyl: ##STR400## the compounds Ia398,in particular the compounds Ia398.001-Ia398.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is phenylsulfonyl and R¹³ is methyl: ##STR401## thecompounds Ia399, in particular the compounds Ia399.001-Ia399.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-butyl, R¹² is phenylsulfonyl and R¹³ is methyl: ##STR402## thecompounds Ia400, in particular the compounds Ia400.001-Ia400.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is iso-butyl, R¹² is phenylsulfonyl and R¹³ is methyl: ##STR403##the compounds Ia401, in particular the compounds Ia401.001-Ia402.180[sic], which differ from the corresponding compounds Ia1.001-Ia1.180 bythe fact that R¹² is 4-methylphenylsulfonyl and R¹³ is methyl:##STR404## the compounds Ia402, in particular the compoundsIa402.001-Ia402.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl, R¹² is4-methylphenylsulfonyl and R¹³ is methyl: ##STR405## the compoundsIa403, in particular the compounds Ia403.001-Ia403.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is 4-methylphenylsulfonyl and R¹³ is methyl: ##STR406##the compounds Ia404, in particular the compounds Ia404.001-Ia404.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is n-butyl, R¹² is 4-methylphenylsulfonyl and R¹³ ismethyl: ##STR407## the compounds Ia405, in particular the compoundsIa405.001-Ia405.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl, R¹² is4-methylphenylsulfonyl and R¹³ is methyl: ##STR408## the compoundsIa406, in particular the compounds Ia406.001-Ia406.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹² isn-propylcarbonyl and R¹³ is methyl: ##STR409## the compounds Ia407, inparticular the compounds Ia407.001-Ia407.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl,R¹² is n-propylcarbonyl and R¹³ is methyl: ##STR410## the compoundsIa408, in particular the compounds Ia408.001-Ia408.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is n-propylcarbonyl and R¹³ is methyl: ##STR411## thecompounds Ia409, in particular the compounds Ia409.001-Ia409.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-butyl, R¹² is n-propylcarbonyl and R¹³ is methyl: ##STR412##the compounds Ia410, in particular the compounds Ia410.001-Ia410.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is iso-butyl, R¹² is n-propylcarbonyl and R¹³ is methyl:##STR413## the compounds Ia411, in particular the compoundsIa411.001-Ia411.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is trifluoromethylcarbonyl and R¹³is methyl: ##STR414## the compounds Ia412, in particular the compoundsIa412.001-Ia412.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl, R¹² istrifluoromethylcarbonyl and R¹³ is methyl: ##STR415## the compoundsIa413, in particular the compounds Ia413.001-Ia413.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is trifluoromethylcarbonyl and R¹³ is methyl: ##STR416##the compounds Ia414, in particular the compounds Ia414.001-Ia414.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is n-butyl, R¹² is trifluoromethylcarbonyl and R¹³ ismethyl: ##STR417## the compounds Ia415, in particular the compoundsIa415.001-Ia415.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl, R¹² istrifluoromethylcarbonyl and R¹³ is methyl: ##STR418## the compoundsIa416, in particular the compounds Ia416.001-Ia416.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹² ismethylsulfonyl and R¹³ is methyl: ##STR419## the compounds Ia417, inparticular the compounds Ia417.001-Ia417.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl,R¹² is methylsulfonyl and R¹³ is methyl: ##STR420## the compounds Ia418,in particular the compounds Ia418.001-Ia418.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is methylsulfonyl and R¹³ is methyl: ##STR421## thecompounds Ia419, in particular the compounds Ia419.001-Ia419.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-butyl, R¹² is methylsulfonyl and R¹³ is methyl: ##STR422## thecompounds Ia420, in particular the compounds Ia420.001-Ia420.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is iso-butyl, R¹² is methylsulfonyl and R¹³ is methyl: ##STR423##the compounds Ia421, in particular the compounds Ia421.001-Ia421.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹² is ethylsulfonyl and R¹³ is methyl: ##STR424## thecompounds Ia422, in particular the compounds Ia422.001-Ia422.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl, R¹² is ethylsulfonyl and R¹³ is methyl: ##STR425## thecompounds Ia423, in particular the compounds Ia423.001-Ia423.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-propyl, R¹² is ethylsulfonyl and R¹³ is methyl: ##STR426## thecompounds Ia424, in particular the compounds Ia424.001-Ia424.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-butyl, R¹² is ethylsulfonyl and R¹³ is methyl: ##STR427## thecompounds Ia425, in particular the compounds Ia425.001-Ia425.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is iso-butyl, R¹² is ethylsulfonyl and R¹³ is methyl: ##STR428## thecompounds Ia426, in particular the compounds Ia426.001-Ia426.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹² is n-propylsulfonyl and R¹³ is methyl: ##STR429## the compoundsIa427, in particular the compounds Ia427.001-Ia427.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isethyl, R¹² is n-propylsulfonyl and R¹³ is methyl: ##STR430## thecompounds Ia428, in particular the compounds Ia428.001-Ia428.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-propyl, R¹² is n-propylsulfonyl and R¹³ is methyl: ##STR431##the compounds Ia429, in particular the compounds Ia429.001-Ia429.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is n-butyl, R¹² is n-propylsulfonyl and R¹³ is methyl:##STR432## the compounds Ia430, in particular the compoundsIa430.001-Ia430.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl, R¹² is propylsulfonyland R¹³ is methyl: ##STR433## the compounds Ia431, in particular thecompounds Ia431.001-Ia431.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹² is iso-propylsulfonyl andR¹³ is methyl: ##STR434## the compounds Ia432, in particular thecompounds Ia432.001-Ia432.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl, R¹² isiso-propylsulfonyl and R¹³ is methyl: ##STR435## the compounds Ia433, inparticular the compounds Ia433.001-Ia433.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is iso-propylsulfonyl and R¹³ is methyl: ##STR436## thecompounds Ia434, in particular the compounds Ia434.001-Ia434.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-butyl, R¹² is iso-propylsulfonyl and R¹³ is methyl: ##STR437##the compounds Ia435, in particular the compounds Ia435.001-Ia435.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is iso-butyl, R¹² is iso-propylsulfonyl and R¹³ is methyl:##STR438## the compounds Ia436, in particular the compoundsIa436.001-Ia436.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is n-butylsulfonyl and R¹³ ismethyl: ##STR439## the compounds Ia437, in particular the compoundsIa437.001-Ia437.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl, R¹² is n-butylsulfonyland R¹³ is methyl: ##STR440## the compounds Ia438, in particular thecompounds Ia438.001-Ia438.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-propyl, R¹² isn-butylsulfonyl and R¹³ is methyl: ##STR441## the compounds Ia439, inparticular the compounds Ia439.001-Ia439.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is n-butyl,R¹² is n-butylsulfonyl and R¹³ is methyl: ##STR442## the compoundsIa440, in particular the compounds Ia440.001-Ia440.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isiso-butyl, R¹² is n-butylsulfonyl and R¹³ is methyl: ##STR443## thecompounds Ia441, in particular the compounds Ia441.001-Ia441.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹² is iso-butylsulfonyl and R¹³ is methyl: ##STR444## the compoundsIa442, in particular the compounds Ia442.001-Ia442.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isethyl, R¹² is iso-butylsulfonyl and R¹³ is methyl: ##STR445## thecompounds Ia443, in particular the compounds Ia443.001-Ia443.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-propyl, R¹² is iso-butylsulfonyl and R¹³ is methyl: ##STR446##the compounds Ia444, in particular the compounds Ia444.001-Ia444.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is n-butyl, R¹² is iso-butylsulfonyl and R¹³ is methyl:##STR447## the compounds Ia445, in particular the compoundsIa445.001-Ia445.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl, R¹² isiso-butylsulfonyl and R¹³ is methyl: ##STR448## the compounds Ia446, inparticular the compounds Ia446.001-Ia446.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹² issec-butylsulfonyl and R¹³ is methyl: ##STR449## the compounds Ia447, inparticular the compounds Ia447.001-Ia447.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ is ethyl,R¹² is sec-butylsulfonyl and R¹³ is methyl: ##STR450## the compoundsIa448, in particular the compounds Ia448.001-Ia448.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is sec-butylsulfonyl and R¹³ is methyl: ##STR451## thecompounds Ia449, in particular the compounds Ia449.001-Ia449.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is n-butyl, R¹² is sec-butylsulfonyl and R¹³ is methyl: ##STR452##the compounds Ia450, in particular the compounds Ia450.001-Ia450.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is iso-butyl, R¹² is sec-butylsulfonyl and R¹³ is methyl:##STR453## the compounds Ia451, in particular the compoundsIa451.001-Ia451.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹² is trifluoromethylsulfonyl and R¹³is methyl: ##STR454## the compounds Ia452, in particular the compoundsIa452.001-Ia452.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is ethyl, R¹² istrifluoromethylsulfonyl and R¹³ is methyl: ##STR455## the compoundsIa453, in particular the compounds Ia453.001-Ia453.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isn-propyl, R¹² is trifluoromethylsulfonyl and R¹³ is methyl: ##STR456##the compounds Ia454, in particular the compounds Ia454.001-Ia454.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is n-butyl, R¹² is trifluoromethylsulfonyl and R¹³ ismethyl: ##STR457## the compounds Ia455, in particular the compoundsIa455.001-Ia455.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is iso-butyl, R¹² istrifluoromethylsulfonyl and R¹³ is methyl: ##STR458## the compoundsIa456, in particular the compounds Ia456.001-Ia456.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹and R¹³ are methyl and R¹² is phenylcarbonylmethyl: ##STR459## thecompounds Ia457, in particular the compounds Ia457.001-Ia457.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹¹ is ethyl, R¹² is phenylcarbonylmethyl and R¹³ is methyl: ##STR460##the compounds Ia458, in particular the compounds Ia458.001-Ia458.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹¹ is n-propyl, R¹² is phenylcarbonylmethyl and R¹³ ismethyl: ##STR461## the compounds Ia459, in particular the compoundsIa459.001-Ia459.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹¹ is n-butyl, R¹² isphenylcarbonylmethyl and R¹³ is methyl: ##STR462## the compounds Ia460,in particular the compounds Ia460.001-Ia460.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹¹ isiso-butyl, R¹² is phenylcarbonylmethyl and R¹³ is methyl: ##STR463## thecompounds Ia461, in particular the compounds Ia461.001-Ia461.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro and R¹³ is methyl: ##STR464## the compounds Ia462, inparticular the compounds Ia462.001-Ia462.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is ethyl and R¹³ is methyl: ##STR465## the compounds Ia463, inparticular the compounds Ia463.001-Ia463.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl and R¹³ is methyl: ##STR466## the compounds Ia464, inparticular the compounds Ia464.001-Ia464.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-butyl and R¹³ is methyl: ##STR467## the compounds Ia465, inparticular the compounds Ia465.001-Ia465.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is iso-butyl and R¹³ is methyl: ##STR468## the compounds Ia466, inparticular the compounds Ia466.001-Ia466.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro andR¹² and R¹³ are methyl: ##STR469## the compounds Ia467, in particularthe compounds Ia467.001-Ia467.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl andR¹² and R¹³ are methyl: ##STR470## the compounds Ia468, in particularthe compounds Ia468.001-Ia468.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyland R¹² and R¹³ are methyl: ##STR471## the compounds Ia469, inparticular the compounds Ia469.001-Ia469.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-butyl and R¹² and R¹³ are methyl: ##STR472## the compoundsIa470, in particular the compounds Ia470.001-Ia470.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is iso-butyl and R¹² and R¹³ are methyl: ##STR473## thecompounds Ia471, in particular the compounds Ia471.001-Ia471.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹² is ethyl and R¹³ is methyl: ##STR474## the compoundsIa472, in particular the compounds Ia472.001-Ia472.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ and R¹² are ethyl and R¹³ is methyl: ##STR475## the compoundsIa473, in particular the compounds Ia473.001-Ia473.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-propyl, R¹² is ethyl and R¹³ is methyl: ##STR476## thecompounds Ia474, in particular the compounds Ia474.001-Ia474.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-butyl, R¹² is ethyl and R¹³ is methyl: ##STR477##the compounds Ia475, in particular the compounds Ia475.001-Ia475.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is iso-butyl, R¹² is ethyl and R¹³ is methyl:##STR478## the compounds Ia476, in particular the compoundsIa476.001-Ia476.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹² is n-propyl and R¹³ ismethyl: ##STR479## the compounds Ia477, in particular the compoundsIa477.001-Ia477.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl, R¹² isn-propyl and R¹³ is methyl: ##STR480## the compounds Ia478, inparticular the compounds Ia478.001-Ia478.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ and R¹² are n-propyl and R¹³ is methyl: ##STR481## the compoundsIa479, in particular the compounds Ia479.001-Ia479.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-butyl, R¹² is n-propyl and R¹³ is methyl: ##STR482## thecompounds Ia480, in particular the compounds Ia480.001-Ia480.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is iso-butyl, R¹² is n-propyl and R¹³ is methyl:##STR483## the compounds Ia481, in particular the compoundsIa481.001-Ia481.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹² is iso-propyl and R¹³is methyl: ##STR484## the compounds Ia482, in particular the compoundsIa482.001-Ia482.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl, R¹² isiso-propyl and R¹³ is methyl: ##STR485## the compounds Ia483, inparticular the compounds Ia483.001-Ia483.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl, R¹² is iso-propyl and R¹³ is methyl: ##STR486## thecompounds Ia484, in particular the compounds Ia484.001-Ia484.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-butyl, R¹² is iso-propyl and R¹³ is methyl:##STR487## the compounds Ia485, in particular the compoundsIa485.001-Ia485.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl, R¹² isiso-propyl and R¹³ is methyl: ##STR488## the compounds Ia486, inparticular the compounds Ia486.001-Ia486.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹² is n-butyl and R¹³ is methyl: ##STR489## the compounds Ia487, inparticular the compounds Ia487.001-Ia487.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is ethyl, R¹² is n-butyl and R¹³ is methyl: ##STR490## the compoundsIa488, in particular the compounds Ia488.001-Ia488.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-propyl, R¹² is n-butyl and R¹³ is methyl: ##STR491## thecompounds Ia489, in particular the compounds Ia489.001-Ia489.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ and R¹² are n-butyl and R¹³ is methyl: ##STR492## thecompounds Ia490, in particular the compounds Ia490.001-Ia490.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is iso-butyl, R¹² is n-butyl and R¹³ is methyl:##STR493## the compounds Ia491, in particular the compoundsIa491.001-Ia491.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹² is sec-butyl and R¹³is methyl: ##STR494## the compounds Ia492, in particular the compoundsIa492.001-Ia492.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl, R¹² issec-butyl and R¹³ is methyl: ##STR495## the compounds Ia493, inparticular the compounds Ia493.001-Ia493.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl, R¹² is sec-butyl and R¹³ is methyl: ##STR496## thecompounds Ia494, in particular the compounds Ia494.001-Ia494.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-butyl, R¹² is sec-butyl and R¹³ is methyl:##STR497## the compounds Ia495, in particular the compoundsIa495.001-Ia495.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl, R¹² issec-butyl and R¹³ is methyl: ##STR498## the compounds Ia496, inparticular the compounds Ia496.001-Ia496.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹² is iso-butyl and R¹³ is methyl: ##STR499## the compounds Ia497, inparticular the compounds Ia497.001-Ia497.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is ethyl, R¹² is iso-butyl and R¹³ is methyl: ##STR500## thecompounds Ia498, in particular the compounds Ia498.001-Ia498.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-propyl, R¹² is iso-butyl and R¹³ is methyl:##STR501## the compounds Ia499, in particular the compoundsIa499.001-Ia499.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹ I is n-butyl, R¹² isiso-butyl and R¹³ is methyl: ##STR502## the compounds Ia500, inparticular the compounds Ia500.001-Ia500.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ and R¹² are iso-butyl and R¹³ is methyl: ##STR503## the compoundsIa501, in particular the compounds Ia501.001-Ia501.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹² is methylcarbonyl and R¹³ is methyl: ##STR504## the compoundsIa502, in particular the compounds Ia502.001-Ia502.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl, R¹² is methylcarbonyl and R¹³ is methyl: ##STR505##the compounds Ia503, in particular the compounds Ia503.001-Ia503.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is n-propyl, R¹² is methylcarbonyl and R¹³ ismethyl: ##STR506## the compounds Ia504, in particular the compoundsIa504.001-Ia504.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl, R¹² ismethylcarbonyl and R¹³ is methyl: ##STR507## the compounds Ia505, inparticular the compounds Ia505.001-Ia505.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is iso-butyl, R¹² is methylcarbonyl and R¹³ is methyl: ##STR508##the compounds Ia506, in particular the compounds Ia506.001-Ia506.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹² is ethylcarbonyl and R¹³ is methyl:##STR509## the compounds Ia507, in particular the compoundsIa507.001-Ia507.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl, R¹² isethylcarbonyl and R¹³ is methyl: ##STR510## the compounds Ia508, inparticular the compounds Ia508.001-Ia508.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl, R¹² is ethylcarbonyl and R¹³ is methyl: ##STR511## thecompounds Ia509, in particular the compounds Ia509.001-Ia509.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-butyl, R¹² is ethylcarbonyl and R¹³ is methyl:##STR512## the compounds Ia510, in particular the compoundsIa510.001-Ia510.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl, R¹² isethylcarbonyl and R¹³ is methyl: ##STR513## the compounds Ia511, inparticular the compounds Ia511.001-Ia511.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹² is n-propylcarbonyl and R¹³ is methyl: ##STR514## the compoundsIa512, in particular the compounds Ia512.001-Ia512.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl, R¹² is n-propylcarbonyl and R¹³ is methyl:##STR515## the compounds Ia513, in particular the compoundsIa513.001-Ia513.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl, R¹ ² isn-propylcarbonyl and R¹³ is methyl: ##STR516## the compounds Ia514, inparticular the compounds Ia514.001-Ia514.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-butyl, R¹² is n-propylcarbonyl and R¹³ is methyl: ##STR517##the compounds Ia515, in particular the compounds Ia515.001-Ia515.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is iso-butyl, R¹² is n-propylcarbonyl and R¹³is methyl: ##STR518## the compounds Ia516, in particular the compoundsIa516.001-Ia516.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹² istrifluoromethylcarbonyl and R¹³ is methyl: ##STR519## the compoundsIa517, in particular the compounds Ia517.001-Ia517.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl, R¹² is trifluoromethylcarbonyl and R¹³ is methyl:##STR520## the compounds Ia518, in particular the compoundsIa518.001-Ia518.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl, R¹² istrifluoromethylcarbonyl and R¹³ is methyl: ##STR521## the compoundsIa519, in particular the compounds Ia519.001-Ia519.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-butyl, R¹² is trifluoromethylcarbonyl and R¹³ is methyl:##STR522## the compounds Ia520, in particular the compoundsIa520.001-Ia520.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl, R¹² istrifluoromethylcarbonyl and R¹³ is methyl: ##STR523## the compoundsIa521, in particular the compounds Ia521.001-Ia521.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹² is methylsulfonyl and R¹³ is methyl: ##STR524## the compoundsIa522, in particular the compounds Ia522.001-Ia522.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl, R¹² is methylsulfonyl and R¹³ is methyl: ##STR525##the compounds Ia523, in particular the compounds Ia523.001-Ia523.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is n-propyl, R¹² is methylsulfonyl and R¹³ ismethyl: ##STR526## the compounds Ia524, in particular the compoundsIa524.001-Ia524.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl, R¹² ismethylsulfonyl and R¹³ is methyl: ##STR527## the compounds Ia525, inparticular the compounds Ia525.001-Ia525.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is iso-butyl, R¹² is methylsulfonyl and R¹³ is methyl: ##STR528##the compounds Ia526, in particular the compounds Ia526.001-Ia526.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹² is ethylsulfonyl and R¹³ is methyl:##STR529## the compounds Ia527, in particular the compoundsIa527.001-Ia527.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl, R¹² isethylsulfonyl and R¹³ is methyl: ##STR530## the compounds Ia528, inparticular the compounds Ia528.001-Ia528.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl, R¹² is ethylsulfonyl and R¹³ is methyl: ##STR531## thecompounds Ia529, in particular the compounds Ia529.001-Ia529.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is n-butyl, R¹² is ethylsulfonyl and R¹³ is methyl:##STR532## the compounds Ia530, in particular the compoundsIa530.001-Ia530.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl, R¹² isethylsulfonyl and R¹³ is methyl: ##STR533## the compounds Ia531, inparticular the compounds Ia531.001-Ia531.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹² is n-propylsulfonyl and R¹³ is methyl: ##STR534## the compoundsIa532, in particular the compounds Ia532.001-Ia532.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl, R¹² is n-propylsulfonyl and R¹³ is methyl:##STR535## the compounds Ia533, in particular the compoundsIa533.001-Ia533.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl, R¹² isn-propylsulfonyl and R¹³ is methyl: ##STR536## the compounds Ia534, inparticular the compounds Ia534.001-Ia534.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-butyl, R¹² is n-propylsulfonyl and R¹³ is methyl: ##STR537##the compounds Ia535, in particular the compounds Ia535.001-Ia535.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is iso-butyl, R¹² is n-propylsulfonyl and R¹³is methyl: ##STR538## the compounds Ia536, in particular the compoundsIa536.001-Ia536.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹² is iso-propylsulfonyland R¹³ is methyl: ##STR539## the compounds Ia537, in particular thecompounds Ia537.001-Ia537.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl,R¹² is iso-propylsulfonyl and R¹³ is methyl: ##STR540## the compoundsIa538, in particular the compounds Ia538.001-Ia538.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-propyl, R¹² is iso-propylsulfonyl and R¹³ is methyl:##STR541## the compounds Ia539, in particular the compoundsIa539.001-Ia539.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl, R¹² isiso-propylsulfonyl and R¹³ is methyl: ##STR542## the compounds Ia540, inparticular the compounds Ia540.001-Ia540.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is iso-butyl, R¹² is iso-propylsulfonyl and R¹³ is methyl:##STR543## the compounds Ia541, in particular the compoundsIa541.001-Ia541.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹² is n-butylsulfonyl andR¹³ is methyl: ##STR544## the compounds Ia542, in particular thecompounds Ia542.001-Ia542.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl,R¹² is n-butylsulfonyl and R¹³ is methyl: ##STR545## the compoundsIa543, in particular the compounds Ia543.001-Ia543.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-propyl, R¹² is n-butylsulfonyl and R¹³ is methyl:##STR546## the compounds Ia544, in particular the compoundsIa544.001-Ia544.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl, R¹² isn-butylsulfonyl and R¹³ is methyl: ##STR547## the compounds Ia545, inparticular the compounds Ia545.001-Ia545.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is iso-butyl, R¹² is n-butylsulfonyl and R¹³ is methyl: ##STR548##the compounds Ia546, in particular the compounds Ia546.001-Ia546.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹² is iso-butylsulfonyl and R¹³ is methyl:##STR549## the compounds Ia547, in particular the compoundsIa547.001-Ia547.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl, R¹² isiso-butylsulfonyl and R¹³ is methyl: ##STR550## the compounds Ia548, inparticular the compounds Ia548.001-Ia548.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl, R¹² is iso-butylsulfonyl and R¹³ is methyl: ##STR551##the compounds Ia549, in particular the compounds Ia549.001-Ia549.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is n-butyl, R¹² is iso-butylsulfonyl and R¹³is methyl: ##STR552## the compounds Ia550, in particular the compoundsIa550.001-Ia550.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl, R¹² isiso-butylsulfonyl and R¹³ is methyl: ##STR553## the compounds Ia551, inparticular the compounds Ia551.001-Ia551.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹² is sec-butylsulfonyl and R¹³ is methyl: ##STR554## the compoundsIa552, in particular the compounds Ia552.001-Ia552.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl, R¹² is sec-butylsulfonyl and R¹³ is methyl:##STR555## the compounds Ia553, in particular the compoundsIa553.001-Ia553.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl, R¹² issec-butylsulfonyl and R¹³ is methyl: ##STR556## the compounds Ia554, inparticular the compounds Ia554.001-Ia554.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-butyl, R¹² is sec-butylsulfonyl and R¹³ is methyl: ##STR557##the compounds Ia555, in particular the compounds Ia555.001-Ia555.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is iso-butyl, R¹² is sec-butylsulfonyl andR¹³ is methyl: ##STR558## the compounds Ia556, in particular thecompounds Ia556.001-Ia556.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹² istrifluoromethylsulfonyl and R¹³ is methyl: ##STR559## the compoundsIa557, in particular the compounds Ia557.001-Ia557.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is ethyl, R¹² is trifluoromethylsulfonyl and R¹³ is methyl:##STR560## the compounds Ia558, in particular the compoundsIa558.001-Ia558.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl, R¹² istrifluoromethylsulfonyl and R¹³ is methyl: ##STR561## the compoundsIa559, in particular the compounds Ia559.001-Ia559.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-butyl, R¹² is trifluoromethylsulfonyl and R¹³ is methyl:##STR562## the compounds Ia560, in particular the compoundsIa560.001-Ia560.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl, R¹² istrifluoromethylsulfonyl and R¹³ is methyl: ##STR563## the compoundsIa561, in particular the compounds Ia561.001-Ia561.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is methyl, R¹² is phenylcarbonylmethyl and R¹³ is methyl:##STR564## the compounds Ia562, in particular the compoundsIa562.001-Ia562.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl, R¹² isphenylcarbonylmethyl and R¹³ is methyl: ##STR565## the compounds Ia563,in particular the compounds Ia563.001-Ia563.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is n-propyl, R¹² is phenylcarbonylmethyl and R¹³ is methyl:##STR566## the compounds Ia564, in particular the compoundsIa564.001-Ia564.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-butyl, R¹² isphenylcarbonylmethyl and R¹³ is methyl: ##STR567## the compounds Ia565,in particular the compounds Ia565.001-Ia565.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is iso-butyl, R¹² is phenylcarbonylmethyl and R¹³ is methyl:##STR568## the compounds Ia566, in particular the compoundsIa566.001-Ia566.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹² is phenylsulfonyl andR¹³ is methyl: ##STR569## the compounds Ia567, in particular thecompounds Ia567.001-Ia567.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is ethyl,R¹² is phenylsulfonyl and R¹³ is methyl: ##STR570## the compounds Ia568,in particular the compounds Ia568.001-Ia568.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹¹ is ethyl [sic], R¹² is phenylsulfonyl and R¹³ is methyl: ##STR571##the compounds Ia569, in particular the compounds Ia569.001-Ia569.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is nitro, R¹¹ is n-butyl, R¹² is phenylsulfonyl and R¹³ ismethyl: ##STR572## the compounds Ia570, in particular the compoundsIa570.001-Ia570.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl, R¹² isphenylsulfonyl and R¹³ is methyl: ##STR573## the compounds Ia571, inparticular the compounds Ia571.001-Ia571.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ is nitro,R¹² is 4-methylphenylsulfonyl and R¹³ is methyl: ##STR574## thecompounds Ia572, in particular the compounds Ia572.001-Ia572.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is nitro, R¹¹ is ethyl, R¹² is 4-methylphenylsulfonyl and R¹³ ismethyl: ##STR575## the compounds Ia573, in particular the compoundsIa573.001-Ia573.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is n-propyl, R¹² is4-methylphenylsulfonyl and R¹³ is methyl: ##STR576## the compoundsIa574, in particular the compounds Ia574.001-Ia574.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ isnitro, R¹¹ is n-butyl, R¹² is 4-methylphenylsulfonyl and R¹³ is methyl:##STR577## the compounds Ia575, in particular the compoundsIa575.001-Ia575.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is nitro, R¹¹ is iso-butyl, R¹² is4-methylphenylsulfonyl and R¹³ is methyl: ##STR578## the compoundsIa576, in particular the compounds Ia576.001-Ia576.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl and R¹³ is methyl: ##STR579## the compounds Ia577, inparticular the compounds Ia577.001-Ia577.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is ethyl and R¹² [sic] is methyl: ##STR580## thecompounds Ia578, in particular the compounds Ia578.001-Ia578.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-propyl and R¹³ is methyl: ##STR581## thecompounds Ia579, in particular the compounds Ia579.001-Ia579.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl and R¹³ is methyl: ##STR582## thecompounds Ia580, in particular the compounds Ia580.001-Ia580.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is iso-butyl and R¹³ is methyl: ##STR583## thecompounds Ia581, in particular the compounds Ia581.001-Ia581.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl and R¹² and R¹³ are methyl: ##STR584## thecompounds Ia582, in particular the compounds Ia582.001-Ia582.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl and R¹² and R¹³ are methyl:##STR585## the compounds Ia583, in particular the compoundsIa583.001-Ia583.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyland R¹² and R¹³ are methyl: ##STR586## the compounds Ia584, inparticular the compounds Ia584.001-Ia584.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl and R¹² and R¹³ are methyl: ##STR587##the compounds Ia585, in particular the compounds Ia585.001-Ia585.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is iso-butyl and R¹² and R¹³ aremethyl: ##STR588## the compounds Ia586, in particular the compoundsIa586.001-Ia586.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹² is ethyl andR¹³ is methyl: ##STR589## the compounds Ia587, in particular thecompounds Ia587.001-Ia587.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ andR¹² are ethyl and R¹³ is methyl: ##STR590## the compounds Ia588, inparticular the compounds Ia588.001-Ia588.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl, R¹² is ethyl and R¹³ is methyl:##STR591## the compounds Ia589, in particular the compoundsIa589.001-Ia589.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-butyl,R¹² is ethyl and R¹³ is methyl: ##STR592## the compounds Ia590, inparticular the compounds Ia590.001-Ia590.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl, R¹² is ethyl and R¹³ is methyl:##STR593## the compounds Ia591, in particular the compoundsIa591.001-Ia591.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹² is n-propyland R¹³ is methyl: ##STR594## the compounds Ia592, in particular thecompounds Ia592.001-Ia592.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl, R¹² is n-propyl and R¹³ is methyl: ##STR595## the compoundsIa593, in particular the compounds Ia593.001-Ia593.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ and R¹² are n-propyl and R¹³ is methyl: ##STR596##the compounds Ia594, in particular the compounds Ia594.001-Ia594.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is n-butyl, R¹² is n-propyl and R¹³is methyl: ##STR597## the compounds Ia595, in particular the compoundsIa595.001-Ia595.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyl,R¹² is n-propyl and R¹³ is methyl: ##STR598## the compounds Ia596, inparticular the compounds Ia596.001-Ia596.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is iso-propyl and R¹³ is methyl: ##STR599## thecompounds Ia597, in particular the compounds Ia597.001-Ia597.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl, R¹² is iso-propyl and R¹³ is methyl:##STR600## the compounds Ia598, in particular the compoundsIa598.001-Ia598.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyl,R¹² is iso-propyl and R¹³ is methyl: ##STR601## the compounds Ia599, inparticular the compounds Ia599.001-Ia599.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl, R¹² is iso-propyl and R¹³ is methyl:##STR602## the compounds Ia600, in particular the compoundsIa600.001-Ia600.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyl,R¹² is iso-propyl and R¹³ is methyl: ##STR603## the compounds Ia601, inparticular the compounds Ia601.001-Ia601.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is n-butyl and R¹³ is methyl: ##STR604## thecompounds Ia602, in particular the compounds Ia602.001-Ia602.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl, R¹² is n-butyl and R¹³ is methyl:##STR605## the compounds Ia603, in particular the compoundsIa603.001-Ia603.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyl,R¹² is n-butyl and R¹³ is methyl: ##STR606## the compounds Ia604, inparticular the compounds Ia604.001-Ia604.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ and R¹² are n-butyl and R¹³ is methyl: ##STR607##the compounds Ia605, in particular the compounds Ia605.001-Ia605.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is iso-butyl, R¹² is n-butyl and R¹³is methyl: ##STR608## the compounds Ia606, in particular the compoundsIa606.001-Ia606.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹² is sec-butyland R¹³ is methyl: ##STR609## the compounds Ia607, in particular thecompounds Ia607.001-Ia607.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl, R¹² is sec-butyl and R¹³ is methyl: ##STR610## the compoundsIa608, in particular the compounds Ia608.001-Ia608.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl, R¹² is sec-butyl and R¹³ is methyl:##STR611## the compounds Ia609, in particular the compoundsIa609.001-Ia609.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-butyl,R¹² is sec-butyl and R¹³ is methyl: ##STR612## the compounds Ia610, inparticular the compounds Ia610.001-Ia610.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl, R¹² is sec-butyl and R¹³ is methyl:##STR613## the compounds Ia611, in particular the compoundsIa611.001-Ia611.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹² is iso-butyland R¹³ is methyl: ##STR614## the compounds Ia612, in particular thecompounds Ia612.001-Ia612.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isethyl, R¹² is iso-butyl and R¹³ is methyl: ##STR615## the compoundsIa613, in particular the compounds Ia613.001-Ia613.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl, R¹² is iso-butyl and R¹³ is methyl:##STR616## the compounds Ia614, in particular the compoundsIa614.001-Ia614.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-butyl,R¹² is iso-butyl and R¹³ is methyl: ##STR617## the compounds Ia615, inparticular the compounds Ia615.001-Ia615.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ and R¹² are iso-butyl and R¹³ is methyl: ##STR618##the compounds Ia616, in particular the compounds Ia616.001-Ia616.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹² is methylcarbonyl and R¹³ is methyl:##STR619## the compounds Ia617, in particular the compoundsIa617.001-Ia617.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is ethyl, R¹²is methylcarbonyl and R¹³ is methyl: ##STR620## the compounds Ia618, inparticular the compounds Ia618.001-Ia618.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl, R¹² is methylcarbonyl and R¹³ ismethyl: ##STR621## the compounds Ia619, in particular the compoundsIa619.001-Ia619.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-butyl,R¹² is methylcarbonyl and R¹³ is methyl: ##STR622## the compounds Ia620,in particular the compounds Ia620.001-Ia620.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl, R¹² is methylcarbonyl and R¹³ ismethyl: ##STR623## the compounds Ia621, in particular the compoundsIa621.001-Ia621.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹² isethylcarbonyl and R¹³ is methyl: ##STR624## the compounds Ia622, inparticular the compounds Ia622.001-Ia622.180, which differ from thecorresponding compounds Ia1.01-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹³ is ethyl, R¹² is ethylcarbonyl and R¹³ is methyl:##STR625## the compounds Ia623, in particular the compoundsIa623.001-Ia623.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyl,R¹² is ethylcarbonyl and R¹³ is methyl: ##STR626## the compounds Ia624,in particular the compounds Ia624.001-Ia624.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl, R¹² is ethylcarbonyl and R¹³ is methyl:##STR627## the compounds Ia625, in particular the compoundsIa625.001-Ia625.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyl,R¹² is ethylcarbonyl and R¹³ is methyl: ##STR628## the compounds Ia626,in particular the compounds Ia626.001-Ia626.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is n-propylcarbonyl and R¹³ is methyl: ##STR629##the compounds Ia627, in particular the compounds Ia627.001-Ia627.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is ethyl, R¹² is n-propylcarbonyland R¹³ is methyl: ##STR630## the compounds Ia628, in particular thecompounds Ia628.001-Ia628.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-propyl, R¹² is n-propylcarbonyl and R¹³ is methyl: ##STR631## thecompounds Ia629, in particular the compounds Ia629.001-Ia629.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl, R¹² is n-propylcarbonyl and R¹³ ismethyl: ##STR632## the compounds Ia630, in particular the compoundsIa630.001-Ia630.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyl,R¹² is n-propylcarbonyl and R¹³ is methyl: ##STR633## the compoundsIa631, in particular the compounds Ia631.001-Ia631.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is trifluoromethylcarbonyl and R¹³ is methyl:##STR634## the compounds Ia632, in particular the compoundsIa632.001-Ia632.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is ethyl, R¹²is trifluoromethyl- carbonyl and R¹³ is methyl: ##STR635## the compoundsIa633, in particular the compounds Ia633.001-Ia633.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl, R¹² is trifluoromethylcarbonyl and R¹³is methyl: ##STR636## the compounds Ia634, in particular the compoundsIa634.001-Ia634.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-butyl,R¹² is trifluoromethylcarbonyl and R¹³ is methyl: ##STR637## thecompounds Ia635, in particular the compounds Ia635.001-Ia635.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is iso-butyl, R¹² is trifluoromethylcarbonyland R¹³ is methyl: ##STR638## the compounds Ia636, in particular thecompounds Ia636.001-Ia636.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ and R¹² are methylsulfonyland R¹³ is methyl: ##STR639## the compounds Ia637, in particular thecompounds Ia637.001-Ia637.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ and R¹² aremethylsulfonyl, R¹¹ is ethyl and R¹³ is methyl: ##STR640## the compoundsIa638, in particular the compounds Ia638.001-Ia638.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ andR¹² are methylsulfonyl, R¹¹ is n-propyl and R¹³ is methyl: ##STR641##the compounds Ia639, in particular the compounds Ia639.001-Ia639.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ and R¹² are methylsulfonyl, R¹¹ is n-butyl and R¹³ ismethyl: ##STR642## the compounds Ia640, in particular the compoundsIa640.001-Ia640.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ and R¹² are methylsulfonyl, R¹¹ isiso-butyl and R¹³ is methyl: ##STR643## the compounds Ia641, inparticular the compounds Ia641.001-Ia641.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is ethylsulfonyl and R¹³ is methyl: ##STR644## thecompounds Ia642, in particular the compounds Ia642.001-Ia642.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl, R¹² is ethylsulfonyl and R¹³ ismethyl: ##STR645## the compounds Ia643, in particular the compoundsIa643.001-Ia643.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyl,R¹² is ethylsulfonyl and R¹³ is methyl: ##STR646## the compounds Ia644,in particular the compounds Ia644.001-Ia644.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl, R¹² is ethylsulfonyl and R¹³ is methyl:##STR647## the compounds Ia645, in particular the compoundsIa645.001-Ia645.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyl,R¹² is ethylsulfonyl and R¹³ is methyl: ##STR648## the compounds Ia646,in particular the compounds Ia646.001-Ia646.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is n-propylsulfonyl and R¹³ is methyl: ##STR649##the compounds Ia647, in particular the compounds Ia647.001-Ia647.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is ethyl, R¹² is n-propylsulfonyland R¹³ is methyl: ##STR650## the compounds Ia648, in particular thecompounds Ia648.001-Ia648.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-propyl, R¹² is n-propylsulfonyl and R¹³ is methyl: ##STR651## thecompounds Ia649, in particular the compounds Ia649.001-Ia649.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl, R¹² is n-propylsulfonyl and R¹³ ismethyl: ##STR652## the compounds Ia650, in particular the compoundsIa650.001-Ia650.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹ is iso-butyl,R¹² is n-propylsulfonyl and R¹³ is methyl: ##STR653## the compoundsIa651, in particular the compounds Ia651.001-Ia651.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is iso-propylsulfonyl and R¹³ is methyl: ##STR654##the compounds Ia652, in particular the compounds Ia652.001-Ia652.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is ethyl, R¹ ² is iso-propylsulfonyland R¹³ is methyl: ##STR655## the compounds Ia653, in particular thecompounds Ia653.001-Ia653.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-propyl, R¹² is iso-propylsulfonyl and R¹³ is methyl: ##STR656## thecompounds Ia654, in particular the compounds Ia654.001-Ia654.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl, R¹² is iso-propylsulfonyl and R¹³is methyl: ##STR657## the compounds Ia655, in particular the compoundsIa655.001-Ia655.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyl,R¹² is iso-propylsulfonyl and R¹³ is methyl: ##STR658## the compoundsIa656, in particular the compounds Ia656.001-Ia656.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is n-butylsulfonyl and R¹³ is methyl: ##STR659## thecompounds Ia657, in particular the compounds Ia657.001-Ia657.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl, R¹² is n-butylsulfonyl and R¹³ ismethyl: ##STR660## the compounds Ia658, in particular the compoundsIa658.001-Ia658.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyl,R¹² is n-butylsulfonyl and R¹³ is methyl: ##STR661## the compoundsIa659, in particular the compounds Ia659.001-Ia659.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-butyl, R¹² is n-butylsulfonyl and R¹³ ismethyl: ##STR662## the compounds Ia660, in particular the compoundsIa660.001-Ia660.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyl,R¹² is n-butylsulfonyl and R¹³ is methyl: ##STR663## the compoundsIa661, in particular the compounds Ia661.001-Ia661.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is iso-butylsulfonyl and R¹³ is methyl: ##STR664##the compounds Ia662, in particular the compounds Ia662.001-Ia662.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is ethyl, R¹² is iso-butylsulfonyland R¹³ is methyl: ##STR665## the compounds Ia663, in particular thecompounds Ia663.001-Ia663.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-propyl, R¹² is iso-butylsulfonyl and R¹³ is methyl: ##STR666## thecompounds Ia664, in particular the compounds Ia664.001-Ia664.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl, R¹² is iso-butylsulfonyl and R¹³is methyl: ##STR667## the compounds Ia665, in particular the compoundsIa665.001-Ia665.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyl,R¹² is iso-butylsulfonyl and R¹³ is methyl: ##STR668## the compoundsIa666, in particular the compounds Ia666.001-Ia666.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is sec-butylsulfonyl and R¹³ is methyl: ##STR669##the compounds Ia667, in particular the compounds Ia667.001-Ia667.180,which differ from the corresponding compounds Ia1.001-Ia1.180 by thefact that R¹ is methylsulfonyl, R¹¹ is ethyl, R¹² is sec-butylsulfonyland R¹³ is methyl: ##STR670## the compounds Ia668, in particular thecompounds Ia668.001-Ia668.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isn-propyl, R¹² is sec-butylsulfonyl and R¹³ is methyl: ##STR671## thecompounds Ia669, in particular the compounds Ia669.001-Ia669.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl, R¹² is sec-butylsulfonyl and R¹³is methyl: ##STR672## the compounds Ia670, in particular the compoundsIa670.001-Ia670.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is iso-butyl,R¹² is sec-butylsulfonyl and R¹³ is methyl: ##STR673## the compoundsIa671, in particular the compounds Ia671.001-Ia671.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹² is trifluoromethylsulfonyl and R¹³ is methyl:##STR674## the compounds Ia672, in particular the compoundsIa672.001-Ia672.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is ethyl, R¹²is trifluoromethylsulfonyl and R¹³ is methyl: ##STR675## the compoundsIa673, in particular the compounds Ia673.001-Ia673.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl, R¹² is trifluoromethylsulfonyl and R¹³is methyl: ##STR676## the compounds Ia674, in particular the compoundsIa674.001-Ia674.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-butyl,R¹² is trifluoromethylsulfonyl and R¹³ is methyl: ##STR677## thecompounds Ia675, in particular the compounds Ia675.001-Ia675.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is iso-butyl, R¹² is trifluoromethylsulfonyland R¹³ is methyl: ##STR678## the compounds Ia676, in particular thecompounds Ia676.001-Ia676.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ ismethyl, R¹² is phenylcarbonylmethyl and R¹³ is methyl: ##STR679## thecompounds Ia677, in particular the compounds Ia677.001-Ia677.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is ethyl, R¹² is phenylcarbonylmethyl and R¹³is methyl: ##STR680## the compounds Ia678, in particular the compoundsIa678.001-Ia678.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyl,R¹² is phenylcarbonyl- methyl and R¹³ is methyl: ##STR681## thecompounds Ia679, in particular the compounds Ia679.001-Ia679.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl, R¹² is phenylcarbonylmethyl andR¹³ is methyl: ##STR682## the compounds Ia680, in particular thecompounds Ia680.001-Ia680.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isiso-butyl, R¹² is phenylcarbonylmethyl and R¹³ is methyl: ##STR683## thecompounds Ia681, in particular the compounds Ia681.001-Ia681.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹² is phenylsulfonyl and R¹³ is methyl:##STR684## the compounds Ia682, in particular the compoundsIa682.001-Ia682.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is ethyl, R¹²is phenylsulfonyl and R¹³ is methyl: ##STR685## the compounds Ia683, inparticular the compounds Ia683.001-Ia683.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is n-propyl, R¹² is phenylsulfonyl and R¹³ ismethyl: ##STR686## the compounds Ia684, in particular the compoundsIa684.001-Ia684.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-butyl,R¹² is phenylsulfonyl and R¹³ is methyl: ##STR687## the compounds Ia685,in particular the compounds Ia685.001-Ia685.180, which differ from thecorresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is iso-butyl, R¹² is phenylsulfonyl and R¹³ ismethyl: ##STR688## the compounds Ia686, in particular the compoundsIa686.001-Ia686.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹² is4-methylphenylsulfonyl and R¹³ is methyl: ##STR689## the compoundsIa687, in particular the compounds Ia687.001-Ia687.180, which differfrom the corresponding compounds Ia1.001-Ia1.180 by the fact that R¹ ismethylsulfonyl, R¹¹ is ethyl, R¹² is 4-methylphenylsulfonyl and R¹³ ismethyl: ##STR690## the compounds Ia688, in particular the compoundsIa688.001-Ia688.180, which differ from the corresponding compoundsIa1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ is n-propyl,R¹² is 4-methylphenylsulfonyl and R¹³ is methyl: ##STR691## thecompounds Ia689, in particular the compounds Ia689.001-Ia689.180, whichdiffer from the corresponding compounds Ia1.001-Ia1.180 by the fact thatR¹ is methylsulfonyl, R¹¹ is n-butyl, R¹² is 4-methylphenylsulfonyl andR¹³ is methyl: ##STR692## the compounds Ia690, in particular thecompounds Ia690.001-Ia690.180, which differ from the correspondingcompounds Ia1.001-Ia1.180 by the fact that R¹ is methylsulfonyl, R¹¹ isiso-butyl, R¹² is 4-methylphenylsulfonyl and R¹³ is methyl: ##STR693##

Very particular extraordinary preference is given to the compounds ofthe formula Ia' (=I, where R¹ is bonded in position 4 of the phenyl ringand R² in position 2 of the phenyl ring) ##STR694## where R¹ is halogenor C₁ -C₄ -alkylsulfonyl;

R² is halogen or C₁ -C₄ -alkyl, in particular halogen;

R³ is hydrogen or C₁ -C₄ -alkyl, in particular hydrogen;

R⁴ is C₁ -C₆ -alkyl, C₃ -C₆ -alkynyl, it being possible for these twosubstituents to be partially or fully halogenated and/or to contain oneto three of the following groups: phenyl or hetaryl, it being possiblefor these, in turn, to be partially or fully halogenated;

X is oxygen;

R¹¹ is C₁ -C₆ -alkyl;

R¹² is hydrogen;

R¹³ is hydrogen.

The 4-benzoylpyrazoles of the formula I can be obtained by variousroutes, for example by the following processes:

Process A:

Reaction of pyrazoles of the formula II where R¹² =H with an activatedcarboxylic acid IIIα or a carboxylic acid IIIβ which is preferablyactivated in situ, to give the acylation product IV, followed by arearrangement reaction. ##STR695##

L¹ is a nucleophilically displaceable leaving group, such as halogen,eg. bromine, chlorine, hetaryl, eg. imidazolyl, pyridyl, carboxylate,eg. acetate, trifluoroacetate and the like.

The activated carboxylic acid can be employed directly, as in the caseof the carboxylic acid halides, or prepared in situ, eg. withdicyclocarbodiimide, triphenylphosphine/azodicarboxylic ester,2-pyridine disulfite/triphenylphosphine, carbonyldiimidazole and thelike.

If appropriate, it may be advantageous to carry out the acylationreaction in the presence of a base. The reactants and the auxiliary baseare expediently employed in equimolar amounts. Under certaincircumstances, a slight excess of the auxiliary base, for example 1.2 to1.5 mol equivalents, based on II, may be advantageous.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkalimetal carbonates. Examples of solvents which can be used are chlorinatedhydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatichydrocarbons such as toluene, xylene, chlorobenzene, ethers such asdiethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polaraprotic solvents such as acetonitrile, dimethylformamide, dimethylsulfoxide, or esters such as ethyl acetate or mixtures of these.

If carboxylic acid halides are employed as activated carboxylic acidcomponent, it may be expedient to cool the reaction mixture to 0-10° C.when adding this reactant. The mixture is subsequently stirred at20-100° C., preferably at 25-50° C., until the reaction is complete.Work-up is carried out in the customary manner, for example the reactionmixture is poured into water and the product of value is extracted.Solvents which are especially suitable for this purpose are methylenechloride, diethyl ether and ethyl acetate. After the organic phase hasbeen dried and the solvent has been numbered, the ester of the formulaIV is purified, preferably by chromatography. Alternatively, it ispossible to employ the crude enol ester of the formula IV for therearrangement reaction without further purification.

The rearrangement of the enol sters [sic] of the formula IV to give thecompounds of the formula I is expediently carried out at from 20 to 40°C. in a solvent and in the presence of a base and, if appropriate, inthe presence of a cyano compound.

Examples of solvents which can be used are acetonitrile, methylenechloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene ormixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines such as triethylamine, pyridine oralkali metal carbonates such as sodium carbonate, potassium carbonate,which are preferably employed in equimolar amounts or up to a four-foldexcess, based on the ester. Triethylamine or alkali metal carbonates arepreferably used.

Suitable cyano compounds are inorganic cyanides such as sodium cyanide,potassium cyanide and organic cyano compounds such as acetonecyanohydrin, trimethylsily [sic] cyanide. They are employed in an amountof 1 to 50 mol percent, based on the ester. Acetone cyanohydrin ortrimethylsilyl cyanide are preferably employed, for example in an amountof 5 to 15, preferably 10, mol percent based on the ester.

Substances which are especially preferably employed are alkali metalcarbonates such as potassium carbonate in acetonitrile or dioxane.

Work-up can be effected in a manner known per se. For example, thereaction mixture is acidified with dilute mineral acid, such as 5%strength hydrochloric acid or sulfuric acid, [lacuna] extracted with anorganic solvent, eg. methylene chloride, ethyl acetate. The organicextract [sic] can be extracted with 5-10% strength alkali metalcarbonate solution, eg. sodium carbonate or potassium carbonatesolution. The aqueous phase is acidified, and the precipitate whichforms is filtered off with suction and/or extracted with methylenechloride or ethyl acetate, dried and concentrated.

(Examples of the synthesis of esters from hydroxypyrazoles and of therearrangement of the esters are mentioned for example in EP-A 282 944 orU.S. Pat. No. 4,643,757).

Process B:

Reaction of 4-benzoylpyrazoles of the formula I where R¹² =H with acompound of the formula V (where R¹² ≠H): ##STR696##

L² is a nucleophilically displaceable leaving group such as halogen, eg.bromine, chlorine, hetaryl, eg. imidazolyl, pyridyl, carboxylate, eg.acetate, trifluoroacetate, sulfonate, eg. mesylate, triflate and thelike.

The compounds of the formula V can be employed directly, for example inthe case of the alkyl halides, carboxylic acid halides, sulfonylhalides, carboxylic anhydrides and sulfonic anhydrides, or prepared insitu, for example activiated carboxylic acids (by means of carboxylicacid and dicyclohexylcarbodiimide, carbonyldiimidazole and the like).

As a rule, the starting compounds are employed in an equimolar ratio.However, it may also be advantageous to employ one or the othercomponent in an excess.

Where appropriate, it may be advantageous to carry out the reaction inthe presence of a base. The reactants and the auxiliary base areexpediently employed in equimolar amounts in this case. Under certaincircumstances, an excess of the auxiliary base, for example 1.5 to 3 molequivalents, based on II, may be advantageous.

Suitable auxiliary bases are tertiary alkylamines such as triethylamine,pyridine, alkali metal carbonates, eg. sodium carbonate, potassiumcarbonate and alkali metal hydrides, eg. sodium hydride. Substanceswhich are preferably used are triethylamine, pyridine and potassiumcarbonate.

Examples of suitable solvents are chlorinated hydrocarbons such asmethylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, eg.toluene, xylene, chlorobenzene, ethers such as diethyl ether, methyltert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents suchas acetonitrile, dimethylformamide, dimethyl sulfoxide or esters such asethyl acetate, or mixtures of these.

As a rule, the reaction temperature is in the range of from 0° C. to theboiling point of the reaction mixture.

Work-up can be effected in a manner known per se to give the product.

The pyrazoles of the formula II (where R¹² =H), which are used asstarting materials, which have not already been disclosed can beprepared by methods known per se (for example EP-A 240 001, J. Prakt.Chem. 315 (1973), 383).

The benzoic acid derivatives of the formula III are novel, ##STR697##the variables having the following meanings: R¹, R² are hydrogen, nitro,halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, --OR⁵, --OCOR⁶,--OSO₂ R⁶, --SH, --S(O)_(n) R⁷, --SO₂ OR⁵, --SO₂ NR⁵ R⁸, --NR⁸ SO₂ R⁶ or--NR⁸ COR⁶ ;

R³ is hydrogen, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, --OR⁷, --SR⁷ or--NR⁷ R¹⁰ ;

R⁴ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -alkenyl, C₄-C₆ -cycloalkenyl, C₃ -C₆ -alkynyl, --COR⁹, --CO₂ R⁹, --COSR⁹ or --CONR⁸R⁹, it being possible for the abovementioned alkyl, cycloalkyl, alkenyl,cycloalkenyl and alkynyl radicals and R⁹ of the radicals --COR⁹, --CO₂R⁹, --COSR⁹ and --CONR⁸ R⁹ to be partially or fully halogenated and/orto have attached to them one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R¹⁰, --OR¹⁰, --SR¹⁰, --NR⁸ R¹⁰,═NOR¹⁰, --OCOR¹⁰, --SCOR¹⁰, --NR⁸ COR¹⁰, --CO₂ R¹⁰, --COSR¹⁰, --CONR⁸R¹⁰, C₁ -C₄ -alkyliminooxy, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkylcarbonyl,C₁ -C₄ -alkoxy-C₂ -C₆ -alkoxycarbonyl, C₁ -C₄ -alkylsulfonyl,heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy,benzyloxy and hetaryloxy, it being possible for the eight last-mentionedradicals, in turn, to be unsubstituted or substituted;

X is oxygen or NR⁸ ;

n is 0, 1 or 2;

R⁵ is hydrogen, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₂ -C₆-alkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl;

R⁶ is C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl;

R⁷ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₃-C₆ -alkenyl or C₃ -C₆ -alkynyl;

R⁸ is hydrogen or C₁ -C₆ -alkyl;

R⁹ is C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, phenyl or benzyl;

R¹⁰ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆-alkynyl;

R¹⁴ is hydroxyl or a radical which can be removed by hydrolysis.

Examples of radicals which can be removed by hydrolysis are alkoxy,phenoxy, alkylthio and phenylthio radicals which can be substituted,halides, hetaryl radicals which are bonded via nitrogen, amino and iminoradicals which can be substituted, and the like.

Preferred are benzoic acid halides IIIα where L=halogen (=III where R¹⁴=halogen), ##STR698## where the variables R¹ to R⁴ and X have themeanings given under formula III and

L is halogen, in particular chlorine or bromine.

Equally preferred are benzoic acids of the formula IIIβ (=III where R¹⁴=hydroxyl), ##STR699## where the variables R¹ to R⁴ and X have themeanings given under formula III.

Equally preferred are benzoic esters of the formula IIIγ (=III where R¹⁴=C₁ -C₆ -alkoxy), ##STR700## where the variables R¹ to R⁴ and X have themeanings mentioned under formula III and

M is C₁ -C₆ -alkoxy.

With regard to the preferred compounds of the formula III, thestatements made under the compounds of the formula I apply to theradicals R¹ to R⁴ and X.

The compounds of the formula IIIα (where L¹ =halogen) can be synthesizedby a method similar to those known from the literature (cf. L. G.Fieser, M. Fieser "Reagents for Organic Synthesis" (1967), Vol. I, pp.767-769) by reacting benzoic acids of the formula IIIβ with halogenatingagents such as thionyl chloride, thionyl bromide, phosgene, diphosgene,triphosgene, oxalyl chloride and oxalyl bromide.

The benzoic acids of the formula IIIβ can be obtained, inter alia, byhydrolyzing the benzoic esters of the formula IIIγ (where M=C₁ -C₆-alkoxy).

The benzoic esters of the formula IIIγ can be obtained by variousroutes, for example by one of the following processes: ##STR701##

Isophthalic acid derivatives of the formula VII can be obtained byoxidizing aldehydes of the formula VI in a manner known per se (J.March, "Advanced Organic Chemistry", 1985, 3rd Edition, p. 629 et seq.,Wiley-Interscience Publication).

The compounds of the formula VII can first be converted into thecorresponding activated carboxylic acids VIII in which L³ is anucleophilically displaceable leaving group such as halogen, eg.bromine, chlorine, hetaroyl, eg. imidazolyl, pyridyl, carboxylate, eg.acetate, trifluoroacetate and the like, by methods similar to thoseknown from the literature, and the products can subsequently beconverted into the corresponding hydroxamic acid or carbohydrazidederivatives of the formula IX (Australian J. Chem. (1969), 22,1731-1735; ibid (1969), 22, 161-173; J. Org. Chem. (1974), 27,1341-1349).

Alkylation of compounds of the formula IX leads to compounds of theformula IIIγ (where R³ ═OR⁷) in a manner known per se (EP-A 463 989;Synthesis (1983), 220-222; U.S. Pat. No. 4,931,088; J. Org. Chem.(1971), 31, 284-294; J. Chem. Soc. Perk. II (1977), 1080-1084).##STR702##

Compounds of the formula IIIγ are obtained in a manner known per se byreacting aldehydes/ketones of the formula X with "alkoxamines oralkylhydrazines". By processes similar to those known from theliterature, it is possible to react aldehydes/ketones of the formula Xwith hydroxylamine, or hydrazine, respectively, and subsequently toalkylate the product (J. March, "Advanced Organic Chemistry", 1985, 3rdEdition, p. 359, pp. 805-806, Wiley-Interscience Publication).##STR703##

Nitriles of the formula XI can be converted into imino esters byalcoholysis (R⁷ OH) in a manner known per se, and these imino esters canbe converted in a further step with hydroxylamines or hydrazines to givecompounds of the formula IIIγ (J. March, "Advanced Organic Chemistry",1985, 3rd Edition, pp. 792-793, Wiley-Interscience Publication; U.S.Pat. No. 4,965,390).

The nitriles of the formula XI can be synthesized by methods similar tothose known from the literature starting from the correspondingaldehydes VI (J. March, "Advanced Organic Chemistry", 1985, 3rd Edition,pp. 806-807, Wiley-Interscience Publication). Equally, it is possible toobtain nitriles of the formula XI from anilines of the formula XII bymeans of Sandmeyer reaction or from aryl halides of the formula XIII byRosemund/von Braun reaction with metal cyanides, in particular CuCN (J.March, "Advanced Organic Chemistry", 1985, 3rd Edition, p. 594, p. 648,Wiley-Interscience Publication). ##STR704##

The aldehydes of the formula VI can be synthesized from correspondingtoluenes of the formula XIV by processes similar to those known from theliterature, by converting them into the ω-halotoluene XV andsubsequently oxidizing the product (cf. Synth. Commun. 22 (1992),1967-1971). ##STR705##

PREPARATION EXAMPLES4-(2,4-Dichloro-3-ethoxyiminomethylbenzoyl)-2-ethyl-3-hyroxy-pyrazole[sic] (Compound 2.03)

A solution of 1.50 g (0.006 mol) of2,4-dichloro-3-ethoxyimino-methylbenzoic acid, 0.61 g (0.006 mol) of2-ethyl-3-hydroxypyrazole and 1.13 g (0.006 mol) ofdicyclohexylcarbodiimide in 50 ml of dry acetonitrile was stirred for 12hours at room temperature. The precipitate was subsequently filtered offwith suction and the filtrate was taken up in water. This aqueoussolution was extracted with ethyl acetate. The combined organic phaseswere dried and concentrated in vacuo. The residue was taken up in 50 mlof dry acetonitrile, treated with 1.20 g (0.0087 mol) of finelypulverulent calcium carbonate and refluxed for 3.5 hours. After cooling,the solvent was removed in vacuo and the residue was taken up in water.The aqueous phase was brought to pH 1-2 using 10% strength hydrochloricacid solution and extracted with ethyl acetate. The combined organicphases were subsequently washed to neutrality with water and dried, andthe solvent was distilled off in vacuo. This gave 0.70 g of4-(2,4-dichloro-3-ethoxyimino-methylbenzoyl)-2-ethyl-3-hydroxypyrazole,which was purified by precipitating with n-hexane from ethyl acetate.(M.p.: 97-98° C.)

Table 2 below lists not only the above-described benzoyl derivatives ofthe formula I but also others which were, or can be, prepared in asimilar manner.

                                      TABLE 2                                     __________________________________________________________________________                                         Ia                                                                              #STR706##                                 -                                                                                                       Physical data                                              M.p. [° C.];                                                   No. X R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.11 R.sup.12 .sup.1 H NMR                                     [δ in ppm]                                 __________________________________________________________________________    2.01                                                                             O SO.sub.2 CH.sub.3                                                                  Cl H  C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                   H  161-163                                            2.02       O        Cl       Cl      H     CH.sub.2 C.tbd.CH  C.sub.2                                    H.sub.5       H       1.45(t, 3H); 2.53                                                                     (s, 1H);                                        4.05(q, 2H);                                                                    4.86(s, 2H); 7.39                                                             (s, 1H); 7.42(d, 1H);                                                         7.52(d, 1H); 8.32                                                             (s, 1H); 8.59(brs, 1H)                           2.03       O        Cl       Cl      H       C.sub.2 H.sub.5                                             C.sub.2 H.sub.5       H           97-98                                        2.04       O        Cl       Cl      H                                        CH.sub.3       C.sub.2 H.sub.5       H                                              108-109                                     2.05       O        Cl       Cl      H       CH.sub.3      n-C.sub.3                                     H.sub.7      H             168-170                 2.06       O        Cl       Cl      H       CH.sub.3      n-C.sub.4                                     H.sub.9      H             171-176                 2.07       O      SO.sub.2 CH.sub.3     Cl      H       CH.sub.3                                         CH.sub.3       H             190-195                                           2.08       O      SO.sub.2 CH.sub.3     Cl                                       H       C.sub.2 H.sub.5       CH.sub.3                                        H             140-145                          2.09       O      SO.sub.2 CH.sub.3     Cl      H      CH.sub.2 C.sub.6                                  H.sub.5     CH.sub.3       H                                                  130-135                                            2.10       O      SO.sub.2 CH.sub.3     Cl      H      CH.sub.2 C.sub.6                                  H.sub.5     C.sub.2 H.sub.5      H                                            50-55                                              2.11       O      SO.sub.2 CH.sub.3     Cl      H      CH.sub.2 -3-                                       C.sub.2 H.sub.5      H           75-80                                       thienyl                                            2.12       O      SO.sub.2 CH.sub.3     Cl      H      CH.sub.2 -3-                                       CH.sub.3       H             140-145                                         thienyl                                            2.13       O      SO.sub.2 CH.sub.3     Cl      CH.sub.3      CH.sub.3                                        CH.sub.3       H                              2.14       O      SO.sub.2 CH.sub.3     Cl      CH.sub.3      CH.sub.3                                        C.sub.2 H.sub.5      H                        2.15       O      SO.sub.2 CH.sub.3    CH.sub.3      CH.sub.3                                            CH.sub.3       CH.sub.3       H                    2.16       O      SO.sub.2 CH.sub.3    CH.sub.3      CH.sub.3                                            CH.sub.3       C.sub.2 H.sub.5      H                                               Oil                                        __________________________________________________________________________

The syntheses of some starting materials are given hereinbelow:

2-Chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid (Compound3.04)

Step a) 2-Chloro-3-methyl-4-methylthioacetophenone

A solution of 157 g (2 mol) of acetyl chloride in 420 ml of1,2-dichloroethane was added dropwise to a suspension of 286 g (2.14mol) of aluminum trichloride in 420 ml of 1,2-dichloroethane at 15-20°C. A solution of 346 g (2 mol) of 2-chloro-6-methylthiotoluene in 1 l of1,2-dichloroethane was subsequently added dropwise. After the reactionmixture had been stirred for 12 hours, it was poured into a mixture of31 of ice and 11 of concentrated HCl. It was extracted with methylenechloride, and the organic phase was washed with water, dried with sodiumsulfate and concentrated. The residue was distilled in vacuo. This gave256 g (60% of theory) of 2-chloro-3-methyl-4-methylthioacetophenone.

(M.p.: 46° C.)

Step b) 2-Chloro-3-methyl-4-methylsulfonylacetophenone

163.0 g (0.76 mol) of 2-chloro-3-methyl-4-methylthioacetophenone weredissolved in 1.5 1 of glacial acetic acid, 18.6 g of sodium tungstatewere added, and 173.3 g of 30% strength hydrogen peroxide solution wereadded dropwise with cooling. Stirring was continued for 2 days and themixture was subsequently diluted with water. The solid which hadprecipitated was filtered off with suction, washed with water and dried.This gave 164.0 g (88% of theory) of2-chloro-3-methyl-4-methylsulfonylacetophenone.

(M.p.: 110-111° C.)

Step c) 2-Chloro-3-methyl-4-methylsulfonylbenzoic acid 82 g (0.33 mol)of 2-chloro-3-methyl-4-methylsulfonylacetophenone were dissolved in 700ml of dioxane, and 1 l of a 12.5% strength sodium hypochlorite solutionwas added at room temperature. Stirring was subsequently continued for 1hour at 80° C. After cooling, two phases formed, of which the bottomphase was diluted with water and slightly acidified. The solid which hadprecipitated was washed with water and dried. This gave 60 g (73% oftheory) of 2-chloro-3-methyl-4-methylsulfonylbenzoic acid.

(M.p.: 230-231° C.)

Step d) Methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate

100 g (0.4 mol) of 2-chloro-3-methyl-4-methylsulfonylbenzoic acid weredissolved in 1 l of methanol, and gaseous hydrogen chloride was passedin for 5 hours at reflux temperature. The mixture was subsequentlyconcentrated. This gave 88.5 g (84% of theory) of methyl2-chloro-3-methyl-4-methylsulfonylbenzoate.

(M.p.: 107-108° C.)

Step e) Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

82 g (0.31 mol) of methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate are[sic] dissolved in 2 l of tetrachloromethane, and 56 g (0.31 mol) ofN-bromosuccinimide were added, a little at a time, with exposure tolight. The reaction mixture was filtered, the filtrate was concentrated,and the residue was taken up in 200 ml of methyl tert-butyl ether. Thesolution was treated with petroleum ether, and the solid which hadprecipitated was filtered off with suction and dried. This gave 74.5 g(70% of theory) of methyl3-bromomethyl-2-chloro-4-methylsulfonylbenzoate.

(M.p.: 74-75° C.)

Step f) Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate

A solution of 41.0 g (0.12 mol) of methyl3-bromomethyl-2-chloro-4-methylsulfonylbenzoate in 250 ml ofacetonitrile was treated with 42.1 g (0.36 mol) of N-methylmorpholineN-oxide. The batch was stirred for 12 hours at room temperature andsubsequently concentrated, and the residue was taken up in ethylacetate. The solution was extracted with water, dried with sodiumsulfate and concentrated. This gave 31.2 g (94% of theory) of methyl2-chloro-3-formyl-4-methylsulfonylbenzoate

(M.p.: 98-105° C.)

Step g) 2-Chloro-3-formyl-4-methylsulfonylbenzoic acid

A solution of 5.00 g of methyl2-chloro-3-formyl-4-methylsulfonylbenzoate was slowly added dropwise toa solution of 9.60 g (0.072 mol) of lithium iodide and 70 ml of drypyridine at reflux temperature. After the reaction mixture had beenstirred for 2 hours under reflux it was cooled, and the solvent wasremoved in vacuo. The residue was subsequently taken up in water andbrought to pH 1-2 using dilute hydrochloric acid. After the aqueousphase had been extracted with ethyl acetate, the combined organic phaseswere washed to neutrality with water, dried and concentrated. This gave4.00 g of 2-chloro-3-formyl-4-methylsulfonylbenzoic acid (85% yield).

(¹ H NMR (d⁶ -DMSO, δ in ppm): 3.41 (s, 3H); 8.05 (d, 1H); 8.11 (d, 1H);10.49 (s, 1H); 14.21 (s, br., 1H).)

Step h) 2-Chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid

1.63 g (0.017 mol) of ethoxyamine hydrochloride and 1.15 g (0.0085 mol)of finely pulverulent potassium carbonate were stirred for 1 hour in 60ml of dry methanol. 4.00 g (0.015 mol) of2-chloro-3-formyl-4-methylsulfonylbenzoic acid in 40 ml of methanol weresubsequently added. After the mixture was stirred for 12 hours at roomtemperature, the solvent was removed, the residue was taken up in ethylacetate, and the organic phase was washed four times with water. Afterthe mixture had been dried and the solvent distilled off, 3.60 g of2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid were obtained(78% yield).

(M.p.: 155-160° C.)

Alternative

Step g') Methyl 2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoate(Compound 3.01)

1.90 g (0.0195 mol) of ethoxyamine hydrochloride and 1.35 g (0.0097 mol)of finely pulverulent potassium carbonate were stirred for 1 hour atroom temperature in 60 ml of dry methanol, and 4.90 g (0.0177 mol) ofmethyl 2-chloro-3-formyl-4-methylsulfonylbenzoate were subsequentlyadded. After the mixture had been stirred for 8 hours at roomtemperature, the solvent was removed, the residue was taken up in ethylacetate, and the organic phase was washed to neutrality with water,dried and concentrated in vacuo. This gave 5.00 g of methyl2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoate. (Yield 88%).

(¹ H NMR (CDC₃, δ in ppm): 1.34 (t, 3H); 3.29 (s, 3H); 3.98 (s, 3H);4.26 (q, 2H); 7.91 (d, 1H); 8.10 (d, 1H); 8.38 (s, 1H).)

Step h') 2-Chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid

A solution of 4.37 g (0.0137 mol) of methyl2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoate was slowly addeddropwise to 7.29 g (0.055 mol) of lithium iodide in 50 ml of drypyridine. After the mixture had been stirred for 2 hours under reflux,it was cooled, and the solvent was removed in vacuo. The residue wastaken up in water and the mixture was brought to pH 1-2 with dilutehydrochloric acid. After the aqueous phase had been extracted with ethylacetate, the combined organic phases were washed with water, dried andconcentrated in vacuo. This gave 3.70 g of2-chloro-3-ethoxyiminomethyl-4-methylsulfonylbenzoic acid. (Yield 89%).

(M.p.: 155-160° C.)

Methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate

Step a) Methyl 2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate

13.8 g (0.11 mol) of sodium hydrogen phosphate monohydrate in 170 ml ofwater, 49.3 g (0.43 mol) of 30% strength hydrogen peroxide solution and66.2 g (0.59 mol) of 80% strength aqueous sodium chlorite solution wereadded in succession at 5° C. to a solution of 115.3 g (0.42 mol) ofmethyl 2-chloro-3-formyl-4-methylsulfonylbenzoate and 2000 ml ofacetonitrile. The reaction solution was subsequently stirred for 1 hourat 5° C. and for 12 hours at room temperature. The pH was then broughtto 1 using 10% strength hydrochloric acid, and 1500 ml of aqueous 40%strength sodium hydrogen sulfite solution were added. After the mixturehad been stirred for 1 hour at room temperature, the aqueous phase wasextracted three times with ethyl acetate. The combined organic phaseswere washed with sodium hydrogen sulfite solution and dried. After thesolvent had been distilled off, 102.0 g of methyl2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate were obtained.

(¹ H NMR (d⁶ -DMSO, δ in ppm): 3.34 (s, 3H); 3.93 (s, 3H); 8.08 (s, 2H);14.50 (s, br., 1H).)

Step b) Methyl 2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate

Two drops of dimethylformamide and 11.9 g (0.1 mol) of thionyl chloridewere added to a solution of 6.0 g (0.021 mol) of methyl2-chloro-3-hydroxycarbonyl-4-methylsulfonylbenzoate and 50 ml of drytoluene. The solution was refluxed for 4 hours. After the solvent hadbeen removed in vacuo, 6.2 g of methyl2-chloro-3-chlorocarbonyl-4-methylsulfonylbenzoate were obtained.

(¹ H NMR (CDCl₃ ; δ in ppm): 3.21 (s, 3H); 4.02 (s, 3H); 8.02 (d, 1H);8.07 (d, 1H).)

2,4-Dichloro-3-(1'-methoxyimino-1'-(methoxy)methyl)benzoyl chloride(Compound 3.14)

Step a) 2,4-Dichloro-3-methylacetophenone

235.0 g (3.0 mol) of acetyl chloride were added dropwise with stirringat 100° C. in the course of 2 hours to a solution of 502.0 g (3.12 mol)of 2,6-dichlorotoluene and 408.0 g (3.06 mol) of aluminum trichloride.After the mixture had been stirred for 2 hours at 100-105° C. it wascooled, and the reaction mixture was poured onto 3 l of ice and 1 l ofwater. The solid which had precipitated during this process was filteredoff with suction and washed to neutrality with 800 ml of water. Afterdrying at 40° C., 500.0 g of 2,4-dichloro-3-methylacetophenone wereobtained as crude product, which were subsequently distilled under ahigh vacuum.

(Boiling point: 121-128° C. (4 mbar))

Step b) 2,4-Dichloro-3-methyl-benzoic acid

First, 655.2 g (4.1 mol) of bromine and subsequently 203.0 g (1.0 mol)of 2,4-dichloro-3-methylacetophenone in 1300 ml of 1,4-dioxane wereadded dropwise to a solution of 520.0 g (13 mol) of sodium hydroxide in2600 ml of water at 0-10° C. After the mixture had been stirred for 12hours, the organic phase was separated off, the aqueous phase wastreated with a 30% strength solution prepared with sodium pyrosulfiteand water, and the mixture was brought to a pH of 1 with hydrochloricacid. The precipitate which had separated out was filtered off withsuction, washed with water and dried at 60° C. in vacuo. This gave 197.0g of 2,4-dichloro-3-methylbenzoic acid.

(M.p.: 173-175° C.)

Step c) Methyl 2,4-dichloro-3-methylbenzoate

60 ml of concentrated sulfuric acid were added dropwise to a solution of424.0 g (2 mol) of 2,4-dichloro-3-methylbenzoic acid and 1500 ml ofmethanol. After the reaction mixture had been refluxed for 5 hours, itwas cooled and concentrated in vacuo, and the residue was subsequentlytaken up in 1000 ml of methylene chloride. The organic phase was washedwith water, subsequently with 5% strength sodium hydrogen carbonatesolution and then again with water, dried and concentrated in vacuo.This gave 401.0 g of methyl 2,4-dichloro-3-methylbenzoate.

(Boiling point: 103-107° C. (1-1.5 mbar))

Step d) Methyl 3-bromomethyl-2,4-dichlorobenzoate

1.0 g of azobisisobutyronitrile was added to a solution of 84.0 g (0.38mol) of methyl 2,4-dichloro-3-methylbenzoate and 67.6 g (0.38 mol) ofN-bromosuccinimide in 380 ml of carbon tetrachloride. After the reactionmixture had been refluxed for 3.5 hours, it was cooled, and theprecipitate which had formed was filtered off with suction. The filtratewas concentrated in vacuo and the resulting residue was extracted bystirring with methyl tert-butyl ether. This gave 108.0 g of methyl3-bromomethyl-2,4-dichlorobenzoate.

(M.p.: 51-54° C.)

Step e) Methyl 2,4-dichloro-3-formylbenzoate

696.2 g (2.97 mol) of aqueous 50% strength N-methylmorpholine N-oxidesolution were added dropwise under reflux to a solution of 312.0 g (0.99mol) of methyl 3-bromomethyl-2,4-dichlorobenzoate in 2 l ofacetonitrile. After the reaction solution had been stirred for 48 hoursat room temperature, it was stirred into 6 1 of water. The precipitatewhich had separated out was filtered off with suction, washed with waterand dried in vacuo. This gave 141.3 g of methyl2,4-dichloro-3-formylbenzoate.

(¹ H NMR (CDCl₃, δ in ppm): 3.98 (s, 3H); 7.47 (d, 1H); 7.84 (d, 1H);10.48 (s, 1H).)

Step f) Methyl 2,4-dichloro-3-hydroxycarbonylbenzoate

5.9 g (0.043 mol) of sodium dihydrogen phosphate monohydrate in 70 ml ofwater, 20.5 g (0.181 mol) of 30% strength hydrogen peroxide solution and27.3 g (0.241 mol) of 80% strength sodium chlorite solution were addedin succession to a solution of 40.0 g (0.172 mol) of methyl2,4-dichloro-3-formylbenzoate and 500 ml of acetonitrile. The reactionsolution was stirred for 1 hour at 5° C. and for 12 hours at roomtemperature. It was subsequently brought to pH 1 with 10% strengthhydrochloric acid, and 500 ml of 40% strength sodium hydrogen sulfitesolution were added. After the mixture had been stirred for 1 hour atroom temperature, the aqueous phase was extracted three times with ethylacetate, and the combined organic phases were washed with 1.0 l of 10%strength sodium hydrogen sulfite solution and subsequently dried. Afterthe solvent had been distilled off, 40.0 g of methyl2,4-dichloro-3-hydroxycarbonylbenzoate were obtained.

(¹ H NMR (d⁶ -DMSO, δ in ppm): 3.90 (s, 3H); 7.69 (d, 1H); 7.89 (d,1H).)

Step g) Methyl 3-chlorocarbonyl-2,4-dichlorobenzoate

Two drops of dimethylformamide and 11.90 g (0.1 mol) of thionyl chloridewere added to a solution of 5.00 g (0.02 mol) of methyl2,4-dichloro-3-hydroxycarbonylbenzoate and 50 ml of dry toluene. Thesolution was refluxed for 4 hours. After the solvent had been distilledoff, 5.35 g of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate wereobtained.

Step h) Methyl 2,4-dichloro-3-methoxyaminocarbonylbenzoate

4.60 g (0.045 mol) of triethylamine and 3.75 g (0.045 mol) ofmethoxyamine hydrochloride were added to a solution of 5.35 g (0.02 mol)of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate and 100 ml ofdichloromethane. After the reaction solution had been stirred for 12hours at room temperature, it was washed with dilute phosphoric acid,dried and concentrated. The residue obtained was extracted by stirringwith diethyl ether. This gave 4.80 g of methyl2,4-dichloro-3-methoxyaminocarbonylbenzoate.

(M.p.: 162-164° C.)

Step i) Methyl2,4-dichloro-3-(1'-methoxyimino-1'-(methoxy)methyl)benzoate (Compound3.09)

A mixture of 16.0 g (0.058 mol) of methyl2,4-dichloro-3-methoxyaminocarbonylbenzoate and 10.1 g (0.073 mol) ofpotassium carbonate in 300 ml of dimethylformamide was stirred for 30minutes at room temperature. 11.0 g (0.087 mol) of dimethyl sulfate weresubsequently added dropwise, the mixture was stirred for 12 hours atroom temperature, and another 11.0 g of dimethyl sulfate were added.After the mixture had been heated for 6 hours at 60° C., it was cooledand stirred into 2 l of ice-water. Then, the aqueous phase was extractedwith ethyl acetate, the combined organic phases were dried and thesolvent was distilled off in vacuo. After chromatography of the residueon silica gel (eluant:toluene/ethyl acetate=9/1), 2.0 g of methyl2,4-dichloro-3-(1'-methoxyimino-1'-(methoxy)methyl)benzoate wereobtained.

(¹ H NMR (CDCl₃, δ in ppm): 3.43 (s, 3H); 3.58 (s, 3H); 3.92 (s, 3H);7.35 (d, 1H); 7.82 (d, 1H).)

Step j) 2,4-Dichloro-3-(1'-methoxyimino-1'-(methoxy)methyl)benzoic acid(Compound 3.10)

A solution of 2.20 g (0.008 mol) of methyl2,4-dichloro-3-(1'-methoxyimino-1'-(methoxy)methyl)benzoate and 3.00 g(0.075 mol) of sodium hydroxide in 50 ml of water was stirred for 2hours at 80° C. After the reaction mixture had cooled, it was stirredinto 200 ml of ice-water and the pH was brought to 1 using concentratedhydrochloric acid. The aqueous phase was extracted with ethyl acetate,and the combined organic phases were dried and concentrated in vacuo.This gave 2.10 g of2,4-dichloro-3-(1'-methoxyimino-1'-(methoxy)methyl)benzoic acid.

¹ H NMR (d⁶ -DMSO, δ in ppm): 3.53 (s, 3H); 3.72 (s, 3H); 7.74 (d, 1H);7.95 (d, 1H).)

Step k) 2,4-Dichloro-3-(1'-methoxyimino-1'-(methoxy)methyl)benzoylchloride (Compound 3.14)

A solution of 2.10 g (0.0076 mol) of2,4-dichloro-3-(1'-(methoxy)imino-1'-methoxymethyl)benzoic acid and20.00 g of thionyl chloride in 50 ml of dry toluene was stirred for 2hours at 80° C. After the solvent had been removed in vacuo, 2.25 g of2,4-dichloro-3-(1'-methoxyimino-1'-(methoxy)methyl)benzoyl chloride wereobtained.

Methyl 2,4-dichloro-3-propoxyaminocarbonylbenzoate

10.7 g (0.04 mol) of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate in 100ml of methylene chloride were slowly added dropwise at 30° C. to asolution of 4.50 g ((0.04 mol) of propoxyamine hydrochloride and 4.05 g(0.04 mol) of triethylamine in 200 ml of methylene chloride. After thereaction mixture had been stirred for 2 hours at room temperature, itwas washed with dilute phosphoric acid, dried and concentrated. Theresidue obtained was chromatographed on silica gel (eluant:toluene/ethylacetate=9/1). This gave 11.50 g of methyl2,4-dichloro-3-propoxyaminocarbonylbenzoate.

(M.p.: 80-81° C.)

Methyl 3-(4-chlorobenzyloxyaminocarbonyl)-2,4-dichlorobenzoate

10.70 g (0.04 mol) of methyl 3-chlorocarbonyl-2,4-dichlorobenzoate in 50ml of methylene chloride were slowly added dropwise at approximatley 30°C. to a solution of 7.76 g (0.04 mol) of 4-chlorobenzyloxyaminehydrochloride and 4.05 g (0.04 mol) of triethylamine in 200 ml ofmethylene chloride. After the reaction mixture had been stirred for 12hours at room temperature, it was washed with dilute phosphoric acid,dried and concentrated. After the residue had been extracted withstirring with diethyl ether, 19.00 g of methyl3-(4-chlorobenzyloxyaminocarbonyl)-2,4-dichlorobenzoate acid wereobtained.

(M.p.: 120-121° C.)

3-(1'-Methoxyiminoeth-1'-yl)-2-methyl-4-methylsulfonylbenzoic acid(compound 3.22)

Step a) 3-(1'-Methoxyiminoeth-1'-yl)-2-methylaniline

50.0 g (0.335 mol) of 3-amino-2-methylacetophenone, 66.3 g (0.838 mol)of pyridine and 42.0 g (0.503 mol) of O-methylhydroxylaminehydrochloride were stirred at room temperature in 400 ml of ethanol.After the solvent had been removed, the residue was taken up inmethylene chloride, washed with water, dried and evaporated, giving 54.0g (91% of theory) of 3-(1'-methoxyiminoeth-1'-yl)-2-methylaniline.

Step b) 3-(1'-Methoxyiminoeth-1'-yl)-2-methyl-4-rhodanoaniline

50.9 g (0.319 mol) of bromine were added dropwise at from -20 to -15° C.to 54.0 g (0.303 mol) of 3-(1'-methoxyiminoeth-1'-yl)-2-methylaniline,49.3 g (0.479 mol) of sodium bromide and 77.5 g (0.956 mol) of sodiumrhodanide in 300 ml of methanol. After the mixture had been stirred atthis temperature for 30 minutes, the insoluble constituents werefiltered off with suction, ethyl acetate was added to the filtrate, andthe pH of the mixture was adjusted to 8 using aqueous sodium bicarbonatesolution. The organic phase was separated off, and the aqueous phaseremaining was extracted several times with ethyl acetate. The combinedorganic phases were then washed with water, dried and evaporated, giving67.3 g (95% of theory) of3-(1'-methoxyiminoeth-1'-yl)-2-methyl-4-rhodanoaniline.

Step c) 3-(1'-Methoxyiminoeth-1'-yl)-2-methyl-4-methylthioaniline

67.3 g (0.286 mol) of3-(1'-methoxyiminoeth-1'-yl)-2-methyl-4-rhodanoaniline in 600 ml ofmethanol were added dropwise at from 20 to 30° C. to 40.4 g (0.315 mol)of sodium sulfide in 200 ml of water. After the mixture had been stirredat room temperature for 3 hours, 45.1 g (0.318 mol) of methyl iodide in200 ml of methanol were added, likewise at from 20 to 30° C. The mixturewas then stirred at room temperature for 12 hours, the solvent wasremoved, and the residue was taken up in water and extracted severaltimes with ethyl acetate. The combined organic phases were then washedwith water, dried and evaporated, and the resultant residue was digestedin n-hexane/methyl tert-butyl ether, giving 43.2 g (67% of theory) of3-(1'-methoxyiminoeth-1'-yl)-2-methyl-4-methylthioaniline.

(m.p. 83-89° C.)

Step d) 6-Bromo-2-(1'-methoxyiminoeth-1'-yl)-3-methylthiotoluene

9.23 g of 47% strength hydrobromic acid were added dropwise at roomtemperature to 3.00 g (13.4 mmol) of3-(1'-methoxyiminoeth-1'-yl)-2-methyl-4-methylthioaniline in 13.40 g ofglacial acetic acid. 9.23 g of water were then added, the mixture wasstirred at room temperature for 10 minutes, and 0.92 g (13.4 mmol) ofsodium nitrite in 1.9 ml of water was added at from -5 to 0° C. Theresultant reaction mixture was then added dropwise at 0° C. to 1.92 g(13.4 mmol) of copper(I) bromide in 6 ml of 47% strength hydrobromicacid. The mixture was stirred at room temperature for 12 hours, pouredinto ice-water and extracted with methylene chloride. The organic phasewas then washed with sodium sulfite solution and water and dried, andthe solvent was removed, giving 2.50 g (65% of theory) of6-bromo-2-(1'-methoxyiminoeth-1'-yl)-3-methylthiotoluene.

Step e) 6-Bromo-2-(1'-methoxyiminoeth-1'-yl)-3-methylsulfonyltoluene

A total of 7.0 g (34.80 mmol) of m-chloroperbenzoic acid were added inportions over the course of 96 hours to 2.5 g (8.71 mmol) of6-bromo-2-(1'-methoxyimino-1'-yl)-3-methylthiotoluene in 50 ml ofmethylene chloride. The solvent was removed, the residue was taken up inan organic solvent, and the solution was washed with sodium carbonatesolution, sodium sulfite solution and water, dried and evaporated. Theresidue was then chromatographed on silica gel (eluent:toluene/ethylacetate), giving 0.8 g (29% of theory) of6-bromo-2-(1'-methoxyiminoeth-1'-yl)-3-methylsulfonyltoluene.

Step f) 3-(1'-Methoxyiminoeth-1'-yl)-2-methyl-4-methylsulfonylbenzoicacid

0.77 g (2.41 mmol) of6-bromo-2-(1'-methoxyiminoeth-1'-yl)-3-methylsulfonyltoluene, 0.03 g(0.1 mmol) of palladium acetate, 0.14 g (0.49 mmol) oftricyclohexylphosphine, 0.10 g (2.4 mmol) of lithium chloride and 0.49 g(4.81 mmol) of triethylamine were suspended in 37.5 ml of toluene and17.5 ml of water and aerated for 36 hours at 140° C. under a pressure of20 bar. After cooling, the insoluble constituents were then separatedoff, the organic phase was extracted with water (to which 1 ml oftriethylamine had been added), and the resultant aqueous phase wasadjusted to pH=1 using hydrochloric acid and extracted with methylenechloride. This organic phase was dried and evaporated, giving 0.62 g(90% of theory) of3-(1'-methoxyiminoeth-1'-yl)-2-methyl-4-methylsulfonylbenzoic acid.

Other benzoic acid derivatives of the formula IIIa which were, or canbe, prepared in a similar manner are listed in Table 3 below in additionto the compounds described above.

                                      TABLE 3                                     __________________________________________________________________________                                        IIIa                                                                            #STR707##                                  -                                                                                                       M.p. [° C.]                                 No. X R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.14 .sup.1 H NMR [ppm]           __________________________________________________________________________    3.01                                                                             O  SO.sub.2 CH.sub.3                                                                  Cl H   C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                         1.34(t, 3H); 3.29                                                                                    (s, 3H); 3.98(s, 3H);                                                         4.26(q, 2H); 7.91                                            (d, 1H); 8.10(d, 1H);                                                                          8.38(s, 1H)                 3.02 O    Cl    Cl   H       CH.sub.3        OCH.sub.3      55-57                                         3.03 O    Cl    Cl   H       C.sub.2                                         H.sub.5       OCH.sub.3     1.35(t, 3H);                                      3.93                                                                                                 (s, 3H); 4.27(q, 2H);                                                         7.42(d, 1H); 7.69                                            (d, 1H); 8.24(s, 1H)                         3.04 O  SO.sub.2 CH.sub.3  Cl   H       C.sub.2 H.sub.5        OH                                        155-160                                            3.05 O    Cl    Cl   H       C.sub.2 H.sub.5        OH      120-123                                       3.06 O    Cl    Cl   H       CH.sub.3                                          OH      168-169                                  3.07 O    Cl    Cl   H      CH.sub.2 C.tbd.CH   OH      155-160                                           3.08 O    Cl    Cl   OC.sub.2 H.sub.5                                        n-C.sub.3 H.sub.7      OH      105-106                                         3.09 O    Cl    Cl   OCH.sub.3    CH.sub.3                                          OCH.sub.3    3.43(s, 3H); 3.58                                               (s, 3H); 3.92(s, 3H);                                                                          7.35(d, 1H); 7.82                                            (d, 1H)                                      3.10 O    Cl    Cl   OCH.sub.3    CH.sub.3         OH      3.53(s, 3H);                                  3.72                                                                                                 (s, 3H); 7.74(d, 1H);                                                         7.95(d, 1H)                 3.11 O    Cl    Cl   OCH.sub.3    CH.sub.2 -4-Cl-C.sub.6 H.sub.4 OH                                       3.55(s, 3H); 5.08                                                                                   (s, 2H); 7.18-7.30                                           (m, 2H); 7.36(d, 1H);                                                                          8.03(d, 1H); 9.14                                            (s, br., 1H)                                 3.12 O    Cl    Cl   OCH.sub.3    n-C.sub.3 H.sub.7      OCH.sub.3                                       47-48                                              3.13 O    Cl    Cl   OC.sub.2 H.sub.5   n-C.sub.3 H.sub.7      OCH.sub.3                                      48-50                                         3.14 O    Cl    Cl   OCH.sub.3    CH.sub.3         Cl                         3.15 O  SO.sub.2 CH.sub.3  Cl     H     CH.sub.2 C.sub.6 H.sub.5                                         OCH.sub.3     95-100                               3.16 O  SO.sub.2 CH.sub.3  Cl     H     CH.sub.2 C.sub.6 H.sub.5     OH                                       115-120                                       3.17 O  SO.sub.2 CH.sub.3  Cl     H     CH.sub.2 -3-thienyl OCH.sub.3                                      90-95                                            3.18 O  SO.sub.2 CH.sub.3  Cl     H     CH.sub.3         OCH.sub.3                                       95-100                                             3.19 O  SO.sub.2 CH.sub.3  Cl     H     CH.sub.3         OH                                              180-185                                            3.20 O  SO.sub.2 CH.sub.3  Cl     H     CH.sub.2 -3-thienyl OH                                           95-100                                             3.21 O  SO.sub.2 CH.sub.3  Cl    CH.sub.3    CH.sub.3         OH                                          3.22 O  SO.sub.2 CH.sub.3  CH.sub.3                                          CH.sub.3    CH.sub.3         OH                  __________________________________________________________________________                                 Oil                                          

The 4-benzoylpyrazoles of the formula I and their agriculturally usefulsalts are suitable as herbicides, both in the form of stereoisomermixtures and in the form of the pure stereoisomers. The herbicidalcompositions comprising compounds of the formula I effect very goodcontrol of vegetation on non-crop areas, especially at high rates ofapplication. In crops such as wheat, rice, maize, soybeans and cottonthey act against broad-leaved weeds and grass weeds without damaging thecrop plants substantially. This effect is observed especially at lowrates of application.

Depending on the application method in question, the 4-benzoylpyrazolesof the formula I, or compositions comprising them, can additionally beemployed in a further number of crop plants for eliminating undesirableplants. Examples of suitable crops are the following: Allium cepa,Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgarisspec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus,Brassica napus var. napobrassica, Brassica rapa var. silvestris,Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citruslimon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffealiberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeisguineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypiumarboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus,Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas,Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersiconlycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musaspec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa,Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylestre[sic], Ricinus communis, Saccharum officinarum, Secale cereale, Solanumtuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifoliumpratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis viniferaand Zea mays.

Moreover, the compounds of the formula I can also be used in crops whichtolerate the action of herbicides due to breeding including geneticengineering methods.

The compounds of the formula I, or the herbicidal compositionscomprising them, can be employed, for example, in the form of directlysprayable aqueous solutions, powders, suspensions, alsohighly-concentrated aqueous, oily or other suspensions or dispersions,emulsions, oil dispersions, pastes, dusts, materials for spreading orgranules, by means of spraying, atomizing, dusting, spreading orpouring. The use forms depend on the intended purposes; in any case,they should guarantee the finest possible distribution of the activeingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount ofat least one compound of the formula I or of an agriculturally usefulsalt of I and auxiliaries conventionally used for the formulation ofcrop protection products.

Suitable inert auxiliaries are essentially: mineral oil fractions ofmedium to high boiling point such as kerosene and diesel oil,furthermore coal tar oils and oils of vegetable or animal origin,aliphatic, cyclic and aromatic hydrocarbons, eg. paraffin,tetrahydronaphthalene, alkylated naphthalenes and their derivatives,alkylated benzenes and their derivatives, alcohols such as methanol,ethanol, propanol, butanol and cyclohexanol, ketones such ascyclohexanone or strongly polar solvents, eg. amines such asN-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates,suspensions, pastes, wettable powders or water-dispersible granules byadding water. To prepare emulsions, pastes or oil dispersions, thesubsrates [sic], as such or dissolved in an oil or solvent, can behomogenized in water by means of wetting agent, tackifier, dispersant oremulsifier. However, it is also possible to prepare concentratescomposed of active substance, wetting agent, tackifier, dispersant oremulsifier and, if appropriate, solvent or oil, and these concentratesare suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal, alkaline earthmetal and ammonium salts of aromatic sulfonic acids, eg. ligno-,phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fattyacids, of alkyl- and alkylaryl sulfonates, of alkyl sulfates, laurylether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-,hepta- and octadecanols, and of fatty alcohol glycol ether, condensatesof sulfonated naphthalene and its derivatives with formaldehyde,condensates of naphthalene, or of the naphthalenesulfonic acids, withphenol and formaldehyde, polyoxyethylene octylphenyl ether, ethoxylatedisooctyl-, octyl- or nonylphenol, alkylphenyl and tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol/ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, laurylalcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite wasteliquors or methylcellulose.

Powders, materials for spreading and dusts can be prepared by mixing orconcommitantly grinding the active substances with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneousgranules, can be prepared by binding the active ingredients to solidcarriers. Solid carriers are mineral earths such as silicas, silicagels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess,clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers such asammonium sulfate, ammonium phosphate, ammonium nitrate, ureas andproducts of vegetable origin such as cereal meal, tree bark meal, woodmeal and nutshell meal, cellulose powders or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-useproducts can be varied within wide ranges. In general, the formulationscomprise approximately from 0.001 to 98% by weight, preferably 0.01 to95% by weight, of at least one active ingredient. The active ingredientsare employed in a purity of from 90% to 100%, preferably 95% to 100%(according to NMR spectrum).

The compounds I according to the invention can be formulated for exampleas follows:

I. 20 parts by weight of the compound No. 2.01 are dissolved in amixture composed of 80 parts by weight of alkylated benzene, 10 parts byweight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleicacid N-monoethanolamide, 5 parts by weight of calciumdodecylbenzenesulfonate and 5 parts by weight of the adduct of mol ofethylene oxide and 1 mol of castor oil. Pouring the solution into100,000 parts by weight of water and finely distributing it thereingives an aqueous dispersion which comprises 0.02% by weight of theactive ingredient.

II. 20 parts by weight of the compound No. 2.03 are dissolved in amixture composed of parts by weight of cyclohexanone, 30 parts by weightof isobutanol, 20 parts by weight of the adduct of 7 mol of ethyleneoxide and 1 mol of isooctylphenol and 10 parts by weight of the adductof 40 mol of ethylene oxide and 1 mol of castor oil. Pouring thesolution into 100,000 parts by weight of water and finely distributingit therein gives an aqueous dispersion which comprises 0.02% by weightof the active ingredient.

III. 20 parts by weight of the active ingredient No. 2.05 are dissolvedin a mixture composed of 25 parts by weight of cyclohexanone, 65 partsby weight of a mineral oil fraction of boiling point 210 to 280° C. and10 parts by weight of the adduct of 40 mol of ethylene oxide and 1 molof castor oil. Pouring the solution into 100,000 parts by weight ofwater and finely distributing it therein gives an aqueous dispersionwhich comprises 0.02% by weight of the active ingredient.

IV. 20 parts by weight of the active ingredient No. 2.06 are mixedthoroughly with 3 parts by weight of sodiumdiisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt ofa lignosulfonic acid from a sulfite waste liquor and 60 parts by weightof pulverulent silica gel and the mixture is ground in a hammer mill.Finely distributing the mixture in 20,000 parts by weight of water givesa spray mixture which comprises 0.1% by weight of the active ingredient.

V. 3 parts by weight of the active ingredient No. 2.01 are mixed with 97parts by weight of finely divided kaolin. This gives a dust whichcomprises 3% by weight of the active ingredient.

VI. 20 parts by weight of the active ingredient No. 2.04 are mixedintimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8parts by weight of fatty alcohol polyglycol ether, 2 parts by weight ofthe sodium salt of a phenol/urea/formaldehyde condensate and 68 parts byweight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound No. 2.03 is dissolved in a mixturecomposed of 70 parts by weight of cyclohexanone, 20 parts by weight ofethoxylated isooctylphenol and 10 parts by weight of ethoxylated castoroil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound No. 2.05 is dissolved in amixture composed of 80 parts by weight of cyclohexanone and 20 parts byweight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylatedcastor oil). This gives a stable emulsion concentrate.

The active ingredients I, or the herbicidal compositions, can be appliedpre- or post-emergence. If the active ingredients are less welltolerated by certain crop plants, application techniques may be used inwhich the herbicidal compositions are sprayed, with the aid of the sprayapparatus, in such a way that they come into as little contact, if any,with the leaves of the sensitive crop plants while reaching the leavesof undesirable plants which grow underneath, or the bare soil(post-directed, lay-by).

To widen the spectrum of action and to achieve synergistic effects, thecompounds of the formula I can be mixed and applied jointly with a largenumber of representatives of other groups of herbicidal orgrowth-regulatory active ingredients. Suitable components in mixturesare, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides,aminophosphoric acid and its derivatives, aminotriazoles, anilides,hetaryloxyalkanoic acid [sic] and its derivatives, benzoic acid and itsderivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetarylaryl ketones, benzylisoxazolidinones, meta-CF₃ -phenylderivatives,carbamates, quinolinecarboxylic acid and its derivatives,chloroacetanilides, cyclohexenone oxime ether derivatives, diazines,dichloropropionic acid and its derivatives, dihydrobenzofurans,dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers,dipyridyls, halocarboxylic acids and their derivatives, ureas,3-phenyluracils, imidazoles, imidazolinones,N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols,aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid andits derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles,phenylpyrazoles, pyridazines, pyridinecarboxylic acid and itsderivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines,triazinones, triazolinones, triazolecarboxamides and uracils.

Moreover, it may be advantageous to apply the compounds the formula I,alone or in combination with other herbicides, in the form of a mixturewith additional other crop protection agents, for example with agentsfor controlling pests, phytopathogenic fungi or bacteria. Also ofinterest is the miscibility with mineral salt solutions which areemployed for treating nutritional and trace element deficiencies.Non-phytotoxic oils and oil concentrates can also be added.

Depending on the intended purpose, the season, the target plants and thegrowth stage, the rates of application of active ingredient are 0.001 to3.0, preferably 0.01 to 1.0, kg/ha active substance (a.s.)

USE EXAMPLES

The herbicidal action of the 4-benzoylpyrazoles of the formula I wasdemonstrated by greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, suspended oremulsified in water, were applied directly after sowing by means offinely distributing nozzles. The containers were irrigated gently topromote germination and growth and subsequently covered with translucentplastic hoods until the plants had rooted. This cover causes [sic]uniform germination of the test plants unless this was adverselyaffected by the active ingredients.

For the post-emergence treatment, the test plants were first grown to aplant height of from 3 to 15 cm, depending on the plant habit, and onlythen treated with the active ingredients which had been suspended oremulsified in water. To this end, the test plants were either sowndirectly and grown in the same containers, or they were first grownseparately as seedlings and transplanted into the test containers a fewdays prior to treatment. The rate of application for the post-emergencetreatment was 0.125 and 0.0625 kg/ha a.s. (active substance).

Depending on the species, the plants were kept at from 10-25° C. and20-35° C., respectively. The test period extended over 2 to 4 weeks.During this time, the plants were tended, and their response to theindividual treatments was evaluated.

Evaluation was carried out using a scale of from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialparts, and 0 means no damage or normal course of growth.

The plants used in the greenhouse experiments belonged to the followingspecies:

    ______________________________________                                        Scientific name   Common name                                                 ______________________________________                                        Chenopodium album lambsquarters (goosefoot)                                     Echinochloa crus galli barnyard grass                                         Sinapis alba           white mustard                                          Setaria faberii        giant foxtail                                          Triticum aestivum      summer wheat                                         ______________________________________                                    

At rates of application of 0.125 and 0.0625 kg/ha (a.s.), compound 2.01(Table 2) was very efficient post-emergence against the abovementionedmono- and dicotyledonous weeds and showed good tolerance in springwheat.

We claim:
 1. A 4-benzoylpyrazole of the formula I ##STR708## where thevariables have the following meanings: R¹, R² are hydrogen, nitro,halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆-alkoxy-C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, --OR⁵, --OCOR⁶,--OSO₂ R⁶, --SH, --S(O)_(n) R⁷, --SO₂ OR⁵, --SO₂ NR⁵ R⁸, --NR⁸ SO₂ R⁶ or--NR⁸ COR⁶ ;R³ is hydrogen, cyano, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl,--OR⁷, --SR⁷ or --NR⁷ R¹⁰ ; R⁴ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆-cycloalkyl, C₃ -C₆ -alkenyl, C₄ -C₆ -cycloalkenyl, C₃ -C₆ -alkynyl,--COR⁹, --CO₂ R⁹, --COSR⁹ or --CONR⁸ R⁹, it being possible for theabovementioned alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynylradicals and R⁹ of the radicals --COR⁹, --CO₂ R⁹, --COSR⁹ and --CONR⁸ R⁹to be partially or fully halogenated and/or to have attached to them oneto three of the following groups:hydroxyl, mercapto, amino, cyano, R¹⁰,--OR¹⁰, --SR¹⁰, --NR⁸ R¹⁰, ═NOR¹⁰, --OCOR¹⁰, --SCOR¹⁰, --NR⁸ COR¹⁰,--CO₂ R¹⁰, --COSR¹⁰, --CONR⁸ R¹⁰, C₁ -C₄ -alkyliminooxy, C₁ -C₄-alkoxyamino, C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-C₂ -C₆-alkoxycarbonyl, C₁ -C₄ -alkylsulfonyl, heterocyclyl, heterocyclyloxy,phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, it beingpossible for the eight last-mentioned radicals, in turn, to besubstituted; X is oxygen or NR⁸ ; n is 0, 1 or 2; R⁵ is hydrogen, C₁ -C₆-alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₃ -C₆ -alkenylor C₃ -C₆ -alkynyl; R⁶ is C₁ -C₆ -alkyl or C₁ -C₆ -haloalkyl; R⁷ is C₁-C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy-C₂ -C₆ -alkyl, C₃ -C₆-alkenyl or C₃ -C₆ -alkynyl; R⁸ is hydrogen or C₁ -C₆ -alkyl; R⁹ is C₁-C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, phenyl or benzyl; R¹⁰ isC₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₃ -C₆ -alkenyl or C₃ -C₆ -alkynyl; Qis a pyrazole of the formula II ##STR709## which is linked in the4-position and where R¹¹ is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, phenyl orphenyl which is partially or fully halogenated and/or has attached to itone to three of the following radicals:nitro, cyano, C₁ -C₄ -alkyl, C₁-C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy; R¹² is hydrogen, C₁-C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkylcarbonyl, C₁ -C₆-haloalkylcarbonyl, C₁ -C₆ -alkoxycarbonyl, C₁ -C₆ -alkylsulfonyl, C₁-C₆ -haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl,phenoxycarbonyl or phenylsulfonyl, the four last-mentioned substituentsbeing unsubstituted or the phenyl ring being in each case partially orfully halogenated and/or having attached to it one to three of thefollowing radicals:nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁-C₄ -alkoxy, C₁ -C₄ -haloalkoxy; R¹³ is hydrogen, C₁ -C₆ -alkyl or C₁-C₆ -haloalkyl;or an agriculturally useful salt thereof.
 2. A4-benzoylpyrazole of the formula I as claimed in claim 1 whereR¹ isnitro, halogen, cyano, thiocyanato, C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl, C₁-C₆ -alkoxy-C₁ -C₆ -alkyl, C₂ -C₆ -alkenyl, C₂ -C₆ -alkynyl, --OR⁵ or--S(O)_(n) R⁷ ; R² is hydrogen or a radical as mentioned above under R¹.3. A 4-benzoylpyrazole of the formula Ia ##STR710## where the variablesR¹ to R⁴, X and Q have the meanings given under claim
 1. 4. A processfor the preparation of 4-benzoylpyrazoles of the formula I as claimed inclaim 1, which comprises acylating a pyrazole of the formula II (whereR¹² =H) where the variables R¹¹ and R¹³ have the meanings given underclaim 1 ##STR711## with an activated carboxylic acid IIIα or with acarboxylic acid IIIβ, ##STR712## where the variables R¹ to R⁴ and X havethe meanings given under claim 1 and L¹ is a nucleophilicallydisplaceable leaving group, subjecting the acylation product to arearrangement reaction, if appropriate in the presence of a catalyst, togive the compounds I (where R¹² =H) and, if desired, to prepare4-benzoylpyrazoles of the formula I where R¹² ≠H reacting the productwith a compound of the formula V

    L.sup.2 R.sup.12                                           V

(where R¹² ≠H) where R¹² has the meanings given under claim 1 with theexception of hydrogen and L² is a nucleophilically displaceable leavinggroup.
 5. A composition comprising a herbicidally active amount of atleast one 4-benzoylpyrazole of the formula I or of an agriculturallyuseful salt of I as claimed in claim 1 and auxiliaries conventionallyused for the formulation of crop protection products.
 6. A process forthe preparation of herbicidally active compositions as claimed in claim5, which comprises mixing a herbicidally active amount of at least one4-benzoylpyrazole of the formula I or of an agriculturally useful saltof I with auxiliaries conventionally used for the formulation of cropprotection products.
 7. A method of controlling undesirable vegetation,which comprises allowing a herbicidally active amount of at least one4-benzoylpyrazole of the formula I or of an agriculturally useful saltof I as claimed in claim 1 to 3 to act on plants, their environmentand/or on seeds.